Tag: M.W=200-300

Reference of 202865-58-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 202865-58-5 name is 1-Bromo-4,5-difluoro-2-methoxybenzene, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Add trifluoromethanesulfonic acid 6-methoxy-1- [4- (2-piperidin-1-yl-ethoxy)- benzoyl] -naphthalen-2-yl ester (2.3 gm, 4.2 mmoles), bis (pinacolato) diboron (1.3 gm, 5.1 mmoles), palladium II acetate (97 mg, 0. 4 mmoles), triphenylphosphine (222 mg, 0.84 mmoles) and cesium fluoride (2.1 gm, 14.1 mmoles) in a 250 ml round bottom flask under nitrogen and add 100 ml of anhydrous acetonitrile. Stir and heat to reflux for 2 hours. Allow the mixture to cool and to this mixture add 2-bromo-4,5-difluoroanisole (2.8 gm, 12.5 mmoles), palladium II acetate (96 mg, 0.43 mmoles) triphenylphosphine (222 mg, 0.84 moles) and cesium fluoride (1.8 gm, 12.2 mmoles). Reflux the mixture for 18 hours and filter through Celite. Evaporate the solvent and pass through an SCX column eluting the product with 2N ammonia/methanol. The product is purified on a silica column eluting with a gradient of 25% THF/hexane to 5% 2N ammonia/methanol in 25 % THF/Hexane. LC/MS gives a peak with the proper mass.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-4,5-difluoro-2-methoxybenzene, and friends who are interested can also refer to it.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/73204; (2005); A1;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 33839-11-1, name is 4-Bromo-2-ethyl-1-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 4-Bromo-2-ethyl-1-methoxybenzene

A mixture of bromide (1.3g, 6. 02MMOL, from step 1), 1-CYCLOPENTYL-2-PROPEN-1-OL (1.14g, 9. 07mmot), DICHLOROBIS (TRIPHENYLPHOSPHINE) PALLADIUM (LL) (85 mg, 0 12 mmol), sodium bicarbonate (0.61 g, 7.25 MMOT) in N-METHYLPYRROLIDINONE (12mL) was heated to 140 C under N2 for 5h. The reaction mixture was partitioned between 1N HCl and EtOAc. The organic layer was washed with saturated NaHCO3, brine, dried over Na2SO4 and concentrated’to a brown oil. The oil was purifed by silica gel chromatography to give the title compound as a yellow oil (0.74g, 47%). 1H NMR (CDCL3): No. ?1. 17 (t, 3H, J = 7.6 Hz), 1. 54-1. 80 (M, 9H), 1.17 (q, 2H, J= 7. 6 HZJ,-2. 73 (m, 2H), 2.84 (m, 2H), 3.80 (s, 3H), 6.75 (d, 1H, J= 8. 0Hz), 6.97 (m, 2H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 33839-11-1.

Reference:
Patent; PFIZER INC.; WO2004/74270; (2004); A2;,
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Synthetic Route of 104750-60-9, The chemical industry reduces the impact on the environment during synthesis 104750-60-9, name is 2-Bromo-1-(methoxymethoxy)-4-methylbenzene, I believe this compound will play a more active role in future production and life.

The bromination of p- cresol, carried out via the method of Narender, et al.,3 was followed by MOM protection 4 (96% yield over two steps). A solution of bis(pinacolato)diborane (2.5 g), dioxane (40 mL), KOAc (2.5 g) and the aryl bromide (6.5 mmol) was purged with nitrogen before Pd(dppf)Cl2 (0.47 g) was added. The mixture was refluxed overnight. Silica chromatography (gradient to 20%) EtOAc/hexanes) gave the boronate ester (1.93 g), which was dissolved in acetone (20 mL) and treated with a solution of Oxone (4 g) in H20 (20 mL). After 10 min, NaHS03 was added and the resulting solution was extracted with EtOAc. Silica chromatography (gradient up to 15% EtOAc/hexanes) gave 2-(methoxymethoxy)-5-methylphenol (0.578 g, 53% over two steps). The diaryl ether was prepared from the phenol and appropriate 4-fluorobenzalde using General Procedure D. Silica chromatography (gradient up to 40% EtOAc/hexanes) gave the intermediate aldehyde (481 mg, 47%). The oxidation was followed by MOM cleavage with cone. HC1 (0.25 mL) in 50% THF/iPrOH (10 mL) to yield 18o (391 mg, 89% over two steps). 1H NMR (CDC13) delta 7.73-7.66 (m, 2H), 6.99-6.85 (m, 3H), 6.76 (s, 1H), 3.97 (s, 3H), 2.24 (s, 3H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-Bromo-1-(methoxymethoxy)-4-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; RESEARCH TRIANGLE INSTITUTE; CARROLL, Frank, I.; THOMAS, James, B.; NAVARRO, Hernan, A.; MASCARELLA, S., Wayne; RUNYON, Scott, P.; JIN, Chunyang; KORMOS, Chad, M.; WO2013/86496; (2013); A2;,
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Related Products of 887267-47-2, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 887267-47-2, name is 2-Bromo-5-(trifluoromethoxy)aniline, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: 3-Bromo-5-(trifluoromethyl)aniline (2.5g, 10.4mmol), 1,4-diazabicyclo [2.2.2]octane (DABCO, 1.4g, 12.5mmol) was dissolved in toluene (40mL). Then 1.9mL carbon disulphide was added dropwise to the above mixture. Subsequently, the mixture was reacted at room temperature for 8h. The product was collected by filtration and dried under vacuum to afford 5 as slight yellow solid (1.2g, 40%).

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-5-(trifluoromethoxy)aniline. I believe this compound will play a more active role in future production and life.

Reference:
Article; Sun, Ying; Shan, Yuanyuan; Li, Chuansheng; Si, Ru; Pan, Xiaoyan; Wang, Binghe; Zhang, Jie; European Journal of Medicinal Chemistry; vol. 141; (2017); p. 373 – 385;,
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68155-69-1, name is 1-Bromo-4-ethoxy-2-methylbenzene, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Quality Control of 1-Bromo-4-ethoxy-2-methylbenzene

Example 11 [Show Image] Synthesis of (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[4-chloro-3-(4-ethoxy-2-methylbenzyl)phenyl]-1-thio-D-glucitol; Five drops of 1,2-dibromoethane were added to a mixture of magnesium (1.11 g, 45.7 mmol), 2-(5-bromo-2-chlorophenyl)-1,3-dioxolane (9.64 g, 36.5 mmol) and tetrahydrofuran (20 mL) and this mixture was heated to reflux for two hours. The reaction mixture was cooled to room temperature, and tetrahydrofuran (15 mL) of 2,3,4,6-tetra-0-benzyl-5-thio-D-glucono-1,5-lactone (10.14 g, 36.5 mmol) was added dropwise to this solution and stirred at room temperature for 30 minutes. After the reaction mixture was added with a saturated ammonium chloride aqueous solution and extracted with ethyl acetate, the organic phase was washed with brine and dried with anhydrous magnesium sulfate. After the desiccant was filtered off, the residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (hexane:ethyl acetate=4:1 to 3:1) to obtain a colorless amorphous 2,3,4,6-tetra-O-benzyl-1-C-[4-chloro-3-(1,3-dioxolan-2-yl)phenyl]-5-thio-D-glucopyranose (11.81 g, 87percent). [Show Image] 1H NMR (300 MHz, CHLOROFORM-d) delta ppm 3.06 (s, 1H) 3.47 – 3.58 (m, 1H) 3.64 (dd, J=10.0, 2.9 Hz, 1H) 3.83 – 4.21 (m, 9H) 4.48 – 4.56 (m, 3 H) 4.66 (d, J=10.6 Hz, 1 H) 4.82 – 4.97 (m, 3 H) 6.15 (s, 1 H) 6.77 (dd, J=7.9, 1.5 Hz, 2 H) 7.08 – 7.21 (m, 5 H) 7.23 – 7.37 (m, 14 H) 7.55 (dd, J=8.4, 2.5 Hz, 1 H) 7:92 (d, J=2.5 Hz, 1 H). Then, 6M hydrochloric acid (120 mL) was added to a tetrahydrofuran (50 mL) solution of 2,3,4,6-tetra-O-benzyl-1-C-[4-chloro-3-(1,3-dioxolane-2-yl)phenyl]-5-thio-D-glucopyranose (6.01 g, 8.12 mmol) while ice-cooled, and stirred at room temperature for two days. The reaction mixture was added with an iced water and extracted with ethyl acetate and the organic phase was washed with a saturated sodium bicarbonate aqueous solution, brine and dried with anhydrous magnesium sulfate. After the desiccant was filtered off, the residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to obtain colorless amorphous 2,3,4,6-tetra-O-benzyl-1-C-(4-chloro-3-formylphenyl)-5-thio-D-glucopyranose (4.53 g, 80percent). [Show Image] 1H NMR (300 MHz, CHLOROFORM-d) delta ppm 3.14 (s, 1 H) 3.43 – 3.58 (m, 1 H) 3.63 (dd, J=10.0, 2.6 Hz, 1 H) 3.87 – 4.16 (m, 5 H) 4.45 – 4.72 (m, 4 H) 4.80 – 5.05 (m, 3 H) 6.73 (d, J=7.8 Hz, 2 H) 7.02 – 7.43 (m, 19 H) 7.74 (dd, J=8.4, 2.5 Hz, 1 H) 8.06 (d, J=2.5 Hz, 1 H) 10.39 (s, 1 H). Then, 2.6 M n-butylithium hexane solution (1.6 mL) was added to a mixture of 1-bromo-4-ethoxy-2-methylbenzene (0.94 g, 4 . 37 mmol) and tetrahydrofuran (12 mL) at -78°C. After stirred for one hour, the mixture was added with a tetrahydrofuran (10 mL) solution of 2,3,4,6-tetra-O-benzyl-1-C-(4-chloro-3-formylphenyl)-5-thio-D-glucopyranose(1.52.g, 2.18 mmol), and, further stirred for 20 minutes, and the reaction mixture was warmed to room temperature. After the reaction mixture was added with a saturated ammonium chloride aqueous solution and extracted with ethyl acetate, the organic phase was washed with brine and dried with anhydrous magnesium sulfate. After the desiccant was filtered off, the residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (hexane:ethyl acetate =2:1) to obtain 2,3,4,6-tetra-O-benzyl-1-C-{4-chloro-3-[(4-ethoxy-2-methylphenyl)(hydroxy)methyl]phenyl}-5-thio-D-glucopyranose (1.72 g, 95percent) as a yellow amorphous diastereomer mixture. Then, an acetonitrile (20 mL) solution of 2,3,4,6-tetra-O-benzyl-1-C-{4-chloro-3-[(4-ethoxy-2-methylphenyl)(hydroxy)methyl]phenyl}-5-thio-D-glucopyranose (1.72 g, 2.06 mmol) was added sequentially with Et3SiH (1.98 mL, 12.4 mmol) and BF3*Et2O (1.04 mL, 8.27 mmol) while cooled on ice. After stirred for one hour, the reaction mixture was warmed up to room temperature and stirred for three hours. After the reaction mixture was added with a saturated sodium carbonate aqueous solution and extracted with ethyl acetate, the organic layer was washed with brine and dried with anhydrous magnesium sulfate. After the desiccant was filtered off, the residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (hexane:ethyl acetate =5:1) to obtain (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[4-chloro-3-(4-ethoxy-2-methylbenzyl)phenyl]-1-thio-D-glucitol (1.01 g, 61percent) as a colorless powder. 1H NMR (300 MHz, CHLOROFORM-d) delta ppm 1.40 (t, J=7.0 Hz, 3 H) 2.14 (s, 3 H) 3.01 – 3.12 (m, 1 H) 3.48 (t, J=8.9 Hz, 1 H) 3.65 – 4.06 (m, 10 H) 4.46 – 4.61 (m, 4 H) 4.80 – 4.91 (m, 3 H) 6.58 (dd, J=8.2, 2.5 Hz, 1 H) 6.68 – 6.76 (m, 2 H) 6.81 (d, J=8.4 Hz, 1 H) 6.98 (d, J=2.2 Hz, 1 H) 7.10 – 7.39 (m, 21 H).

The synthetic route of 68155-69-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD; EP1845095; (2007); A1;,
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35736-52-8, name is 2,4-Dibromo-5-methoxyaniline, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Quality Control of 2,4-Dibromo-5-methoxyaniline

2,4-Dibromo-5-methoxyaniline (930 mg, 3.31 mmol) and paraformaldehyde (160 mg, 5.30 mmol) were dissolved in trifluoroacetic acid (30 mL). The reaction mixture was stirred under an argon atmosphere in dark for 48 h. The reaction mixture was then basified with a solution of concentrated ammonia (30 mL) in water (30 mL). A saturated sodium hydrogen carbonate solution (100 mL) was added and the aqueous mixture was extracted into dichloromethane (3×50 mL). The combined organic layers were washed with brine (100 mL), dried over anhydrous sodium sulfate, filtered and evaporated to dryness. The crude material was chromatographed (silica, dichloromethane) to afford (+/-)-18 (450 mg, 53%) as a pale off-white solid: mp 181-182 C; Rf (CH2Cl2) 0.22; IR (neat) numax 2938, 2895, 2848, 1604, 1486, 1442, 1420, 1247, 1195, 1082 cm-1; 1H NMR (400 MHz, CDCl3) delta 3.74 (s, 3H, OCH3), 3.84 (s, 3H, OCH3), 4.15-4.33 (m, 4H, CH2), 4.47 (d, J 17.0 Hz, 1H, CH2), 4.52 (d, J 17.0 Hz, 1H, CH2), 6.66 (s, 1H, ArH), 7.09 (s, 1H, ArH), 7.61 (s, 1H, ArH); 13C NMR (100 MHz, CDCl3) delta 54.1, 55.3, 56.2, 60.2, 66.5, 107.1, 108.3, 111.5, 114.7, 120.8, 125.5, 131.0, 134.6, 145.4, 147.4, 153.5, 155.0; Anal. Calcd for C17H15Br3N2O2.0.1 CH2Cl2: C 38.93; H 2.90; N 5.31. Found: C 38.85; H 2.73; N 5.06%.

The synthetic route of 35736-52-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Malik, Qasim M.; Ijaz, Sadia; Craig, Donald C.; Try, Andrew C.; Tetrahedron; vol. 67; 32; (2011); p. 5798 – 5805;,
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Related Products of 330-93-8, The chemical industry reduces the impact on the environment during synthesis 330-93-8, name is 4,4′-Oxybis(fluorobenzene), I believe this compound will play a more active role in future production and life.

Step 1 2-Bromo-l , 1 -dimethoxypropaneOMeBr[00297] A solution of propanal (12 5 mL, 170 mmol) m MeOH (85 mL) is stirred at rt and molecular sieves (3 A, powdered, 4 3 g) are added The mixture is heated at reflux, Br2 (8 8 mL, 170 mmol) is added dropwise over 30 mm and reflux is then continued for 4 5 h The mixture is stirred overnight at rt and K2CO3 (11 9 g, 86 mmol) is then added and the resulting slurry is stirred for 2 5 h This is filtered and the solid is washed with MeOH (20 mL) B?ne (100 mL) is added to the filtrate and the mixture is extracted with pentane (3 x 75 mL) The extracts are d?ed over MgSO4 and evaporated under reduced pressure to afford a pale yellow oil (16 0 g) which is not purified further

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4,4′-Oxybis(fluorobenzene), other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GALAPAGOS N.V.; WO2007/131991; (2007); A1;,
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Electric Literature of 1036724-54-5, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 1036724-54-5 as follows.

Six reactions were carried out in parallel and combined for work-up. To a solution of the product of the previous step (200 g, 711 mmol) in THF (100 mL) was added potassium carbonate (197 g, 1.4 mol). The reaction mixture was purged with nitrogen 3 times, followed by addition of Pd(dppf)Cl2-CH2Cl2 (11.6 g, 14.2 mmol). The reaction mixture was cooled to 0 C., diethylzinc (1 M, 1.07 L) was added drop-wise, and the reaction mixture was stirred at 70 C. for 1 h. The reactions were combined, cooled to 20 C. and poured into water (7 L) slowly. To the mixture was added aq. 4 M HCl to pH 6. The organic layer was separated, and the aqueous phase was extracted with EtOAc (3×2 L). The combined organic layer was washed with brine (5 L), dried over sodium sulfate, concentrated, and purified through a silica gel pad (eluted with 50:1 petroleum ether:EtOAc)) to give the title intermediate (900 g, 92% yield) as a light yellow oil. 1H NMR (400 MHz, CDCl3) delta 7.29-7.43 (m, 5H), 6.94-6.97 (m, 1H), 6.82 (d, J=8.0 Hz, 1H), 6.70 (m, 1H), 5.09 (s, 2H), 2.52-2.58 (m, 2H), 1.17 (t, J=7.6 Hz, 3H).

According to the analysis of related databases, 1036724-54-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THERAVANCE BIOPHARMA R&D IP, LLC; Fatheree, Paul R.; Jiang, Lan; US2020/131178; (2020); A1;,
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Electric Literature of 115929-62-9, These common heterocyclic compound, 115929-62-9, name is 3-Bromo-2,5-dimethoxyaniline, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: In a round bottom flask equipped with a magnetic stirring bar, 0.3mmol of alpha-formyl-beta-carboline (1a) and 0.3mmol of aniline (2a) in 4mL of [Bmim][BF4] was stirred for 12min. Into this reaction mixture were added 0.35mmol of phenylacetylene (3a) and 10mol% of La(OTf)3 and then heated around 95-100C. After completion of the reaction, as indicated by the TLC, water was added and extracted with ethylacetate. The organic layer was dried over anhydrous Na2SO4. The solvent was concentrated under the reduced pressure. Product was purified by column chromatography on silica gel (eluent: Hexanes/ethyl acetate): Colorless solid, 126 mg, 74%, Rf=0.52 (20% EtOAc/Hexanes), mp: 277-279 C; IR (KBr): 3356, 2939, 2841, 1259, 1107, 744, 545 cm-1; 1H NMR (400 MHz, CDCl3, TMS) delta: 12.51 (1H, s), 9.01 (1H, s), 8.77 (1H, s), 8.28 (1H, d, J=7.7 Hz), 7.76-7.78 (1H, m), 7.69 (1H, t, J=7.4 Hz), 7.40-7.45 (6H, m), 6.99 (1H, s), 4.31 (3H, s), 4.08 (3H, s), 3.56 (3H, s); 13C NMR (100 MHz, CDCl3, TMS) delta: 166.7, 156.3, 153.2, 149.7, 147.2, 143.3, 141.9, 141.3, 137.3, 137.2, 136.9, 130.8, 129.2, 128.3, 127.2, 127.1, 122.1, 121.6, 121.3, 120.9, 119.0, 118.9, 116.7, 112.3, 110.3 (aromatic C), 61.6, 55.7, 52.6 (aliphatic C); HRMS (ESI-MS) calcd for C30H22BrN3O4; 590.0692 (M+Na), found: 590.0692. Anal. Calcd for: C, 63.39; H, 3.90; N, 7.39%; found: C, 63.25; H, 3.98; N, 7.21%.

Statistics shows that 3-Bromo-2,5-dimethoxyaniline is playing an increasingly important role. we look forward to future research findings about 115929-62-9.

Reference:
Article; Ramesh, Subburethinam; Nagarajan, Rajagopal; Tetrahedron; vol. 69; 24; (2013); p. 4890 – 4898;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 887267-47-2, name is 2-Bromo-5-(trifluoromethoxy)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 887267-47-2

Intermediate 117 4-(Trifluoromethoxy)biphenyl-2-amine 2-Bromo-5-(trifluoromethoxy)aniline (CAS 887267-47-2; 200 mg), phenylboronic acid (143 mg) and a 2 M aqueous solution of sodium carbonate (1.17 ml) were combined at r.t. under argon with dioxane (9.4 ml) and water (3.75 ml). [Iota, – Bis(diphenylphosphino)ferrocene]dichloropalladium(II), dichloromethane adduct (31.9 mg) was added to give yellow suspension. The reaction mixture was heated to 80 C and stirred overnight at 80 C. The reaction mixture was cooled down and filtered through glass fiber paper, washed with 30 mL water and 30 mL EtOAc, the layers were separated, the aqueous layer was back- extracted with EtOAc. The organic layers were combined, dried over MgS04 and concentrated in vacuo. The product was purified by flash chromatography (silical gel, 0% to 70% EtOAc in n- heptane) to give the title compound (198 mg) as a yellow oil.

The synthetic route of 887267-47-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BUETTELMANN, Bernd; CECCARELLI, Simona M.; CONTE, Aurelia; KUEHNE, Holger; KUHN, Bernd; NEIDHART, Werner; OBST SANDER, Ulrike; RICHTER, Hans; WO2014/146994; (2014); A1;,
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