Tag: M.W=200-300

Synthetic Route of 6358-77-6, A common heterocyclic compound, 6358-77-6, name is 5-Bromo-2-methoxyaniline, molecular formula is C7H8BrNO, 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.

Roundbottom flask is charged with 5-bromo-2-methylaniline ( 100.00 mg; 0.54 mmol; 1 .0 eq), methanol (1.5 mL), 37 % formaldehyde solution in methanol (289.18 mg; 3.56 mmol; 2.40 eqf.) and acetic acid (104.68 mg; 1.29 mmol; 2.40 eq.). RM is stirred at room temperature for 10 minutes. After this time RM is cooled down to 0C and sodiumcyanoborohydride (70.93 mg; 1 .13 mmol; 2.10 eqf.) is added. Reaction mixture is stirred in this temperature for 1 h. Then the solvent is evaporated and reaction is quenched with saturated aqueous solution of NaHC03 (5 mL) and extracted with DCM ( 3×5 mL). Combined organic extracts are washed with water (2×10 mL). Organic solvent is then evaporated and crude product is further purified by FCC(DCM/EtOAc, gradient) to 5-bromo-N,N,2-trimethylaniline (74.20 mg; yield 61.6 %; 95.5 % by UPLC) as a colorless oil.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; SELVITA S.A.; FABRITIUS, Charles-Henry Robert Yves; NOWAK, Mateusz Oktawian; WIKLIK, Katarzyna Anna; SABINIARZ, Aleksandra Barbara; BIE?, Marcin Dominik; BUDA, Anna Ma?gorzata; GUZIK, Pawel Szczepan; JAKUBIEC, Krzysztof Roman; MACIUSZEK, Monika; KWIECI?SKA, Katarzyna; TOMCZYK, Mateusz Micha?; GA??ZOWSKI, Micha? Miko?aj; GONDELA, Andrzej; DUDEK, ?ukasz Piotr; (681 pag.)WO2016/180536; (2016); A1;,
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Related Products of 14804-31-0,Some common heterocyclic compound, 14804-31-0, name is 4-Bromo-1-methoxy-2-methylbenzene, molecular formula is C8H9BrO, 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: To a solution of compound 1a-e (10.0 mmol,1.0 eq) in anhydrousTHF (20 mL) was slowly added n-BuLi (6 mL of 2.5 M solution inhexane, 15.0 mmol, 1.5 eq) at 78 C. The mixture was stirred for1 h and triisopropyl borate (50.0 mmol, 5.0 eq) was added by syringe.The solutionwas stirred for another 1 h and allowed towarmto 25 C overnight. The reactionwas cooled to 0 C, followed by thesequential addition ofwater (5 mL) and 2N HCl (5 mL). After 10 min,an additional 35 mL of 2N HCl was added and the mixture wasfurther stirred for 30 min. The mixture was extracted with ethylacetate (20 mL * 3) and the combined organic layers wereconcentrated to a thick oil under reduced pressure. Crystallizationwith cold hexane yielded a white solid.

The synthetic route of 14804-31-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sang, Yali; Han; Pannecouque, Christophe; De Clercq, Erik; Zhuang, Chunlin; Chen; European Journal of Medicinal Chemistry; vol. 182; (2019);,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, A new synthetic method of this compound is introduced below., Recommanded Product: ((3-Bromopropoxy)methyl)benzene

To a suspension of NaH (55 wt percent in oil, 253 mg, 5.8 mmol) in DMF (12 mL) was added 3-bromo-10,11-dihydro-5H-dibenzo[b,f]azepine (9) (1.4 g, 5.1 mmol) in DMF (12 mL) at 0 °C. After stirring for 10 min at room temperature, the mixture was cooled to 0 °C, and then benzyl 3-bromopropyl ether (1.37 g, 5.8 mmol) was added. The mixture was stirred for 1 h at room temperature, then 10percent aq NH4Cl and ethyl acetate were added to the reaction mixture. The mixture was extracted with ethyl acetate 2 times, and the combined extracts were washed with brine, dried over Na2SO4, and the solvent was removed under reduced pressure. The residual paste was chromatographed on silica gel (AcOEt/hexane) to afford (10) as a colorless oil (1.71 g, 79percent yield).1H NMR (CDCl3, delta ppm): 6.85-7.47 (12H, m), 4.43 (2H, s), 3.80 (2H, t, J = 6.4 Hz), 3.46 (2H, t, J = 6.0 Hz), 2.92-3.10 (4H, m), 1.77-1.92 (2H, m).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Kubota, Katsumi; Kurebayashi, Hirotaka; Miyachi, Hirotaka; Tobe, Masanori; Onishi, Masako; Isobe, Yoshiaki; Bioorganic and Medicinal Chemistry; vol. 19; 9; (2011); p. 3005 – 3021;,
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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. 62415-74-1, name is 1,2-Dibromo-4-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 62415-74-1

Add 4-methoxy-o-dibromobenzene (1.0 mmol), thentBuOOH (1.2mmol), Cu (acac) 2 (0.08mmol), then add 2mL of solvent water, and react at room temperature for 8 hours,After the reaction was completed, the reaction solution was concentrated, and the corresponding product was separated by column chromatography, with a separation yield of 91%.

According to the analysis of related databases, 62415-74-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Institute of Technology; Yao Zijian; Qiao Xinchao; (6 pag.)CN110981702; (2020); A;,
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Related Products of 36805-97-7, 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. 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 1-2; Synthesis of Compound 5 (di-tert-butyl ester of (2S, 3S)-N-(tert-butoxycarbonyl)-3-(3,5-dinitrobenzyloxy)aspartic acid) from Compound 3 in Figure 1; To a solution of Compound 3 (455 mg, 0.84 mmol) in methanol (3 mL), a catalytic amount of DL-camphorsulfonic acid was added and stirred at room temperature for 18 hours. After addition of saturated aqueous sodium bicarbonate to stop the reaction, the reaction mixture was extracted with ether and the organic layer was washed with saturated aqueous sodium chloride. After the organic layer was dried over magnesium sulfate, the solvent was distilled off and the resulting residue was dissolved in acetone (5 mL), followed by addition of Jones reagent until brown did not disappear. After stirring at room temperature for 30 minutes, 2-propanol was added to stop the reaction. The reaction mixture was extracted with ether and the organic layer was washed with saturated aqueous sodium chloride. The organic layer was dried over magnesium sulfate and the solvent was distilled off to give carboxylic acid (4) (26 mg, 72% for 2 steps). The thus obtained 4 was dissolved in methanol (2 mL) and 1 N NaOH (2.5 mL) was added thereto under ice cooling, followed by stirring at room temperature for 4 hours. The reaction mixture was adjusted with 2 N hydrochloric acid to pH 1 and extracted with ethyl acetate. The solvent was distilled off and the resulting residue was dissolved in N,N-dimethylformamide di-tert-butylacetal (5 mL) and heated at 90C for 15 minutes. The reaction mixture was cooled on ice and water was added thereto, followed by stirring for 18 hours. After extraction with ether, the organic layer was washed with saturated aqueous sodium chloride and dried over magnesium sulfate. The solvent was distilled off the resulting residue was purified by silica gel column chromatography (ether/hexane = 1/3) to give the titled compound (257 mg, 77% for 2 steps). Oil; [alpha]D -4.2 (c 1.22, CHCl3) ; 1H-NMR (CDCl3, 400 MHz) delta1.39 (s, 9 H), 1.44 (s, 9 H), 1.47 (s, 9 H), 4.51 (d, 1 H, J = 2.5 Hz), 4.58 (d, 1 H, J = 12.5 Hz), 4.81 (dd, 1 H, J = 2.0, 10.5 Hz), 5.03 (d, 1 H, J = 12.5 Hz), 5.19 (d, 1 H, J = 10.5 Hz), 8.50 (d, 2 H, J = 2.0 Hz), 8.93 (t, 1 H, J = 2.0 Hz).

The synthetic route of 1,1-Di-tert-butoxy-N,N-dimethylmethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNTORY LIMITED; EP1849766; (2007); A1;,
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Electric Literature of 36805-97-7, 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. 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

1,1-Di-teit-butoxy-N,N-dimethylmethanamine (6.77 ml, 28.3 mmol) was added to asuspension of 2-({[(benzyloxy)carbonyl]amino}methyl)- 1-ethyl-i H-i, 3-benzodiazole-6- carboxylic acid, Intermediate 4 (2.50 g, 7.08 mmol) in a,a,a-trifluorotoluene (50 ml). The reaction mixture was heated at 100 00 for 1 h. The reaction mixture was allowed to cool to RT then i,i-di-teit-butoxy-N,N-dimethylmethanamine (6.77 ml, 28.3 mmol) was added dropwise over 15 mm. The resultant mixture was heated at 100 00 for 45 mm. Thereaction mixture was cooled to 50 00 then i,i-di-teit-butoxy-N,N-dimethylmethanamine (3.38 ml, 14.2 mmol) was added dropwise over 5 mm. The resultant mixture was heated at 100C for 0.5 h then allowed to cool to RT. The reaction mixture was partitioned between EtOAc (50 ml) and water (50 ml). The phases were separated then the organic phase was washed with water (2 x 30 ml), saturated aqueous NaHCO3 solution (20 ml)and brine (10 ml) then dried over Na2504, filtered and concentrated in vacuo to afford a beige solid (2.5 g). The solid thus obtained was suspended in MeCN (10 ml). The solid was collected by filtration then dried under vacuum to afford the product as an off-white solid (2.30 g, 79%).1H NMR (500 MHz, DMSO-d6) O 8.07 (5, 1H), 7.97 (m, 1H), 7.76 (dd, J= 8.4, 1.5 Hz,1 H), 7.64 (d, J = 8.4 Hz, 1 H), 7.34 (m, 5H), 5.07 (5, 2H), 4.55 (d, J = 6.0 Hz, 2H), 4.38 -4.25 (m, 2H), 1.57 (5, 9H), 1.29 (m, 3H).LC/MS (System A): m/z (ESl) = 410 [MH], R = 1.17 mi UV purity = 99%.

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, 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ENTERPRISE THERAPEUTICS LIMITED; HAY, Duncan, Alexander; SCHOFIELD, Thomas, Beauregard; WENT, Naomi; MCCARTHY, Clive; (108 pag.)WO2019/77340; (2019); A1;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 59557-91-4, name is 4-Bromo-2-methoxyaniline, A new synthetic method of this compound is introduced below., Product Details of 59557-91-4

Add in 100mL single-mouth bottles85% sulfuric acid (39 mL) and 4-bromo-2-methoxyaniline (5 g, 24.8 mmol),The temperature was lowered to 0-5 C, and cerium nitrate (3.2 g, 26.1 mmol) was added in portions.After the addition, the temperature was reacted for 45 minutes.The reaction solution was poured into iced 50% aqueous sodium hydroxide (100 mL, pH > 8).The temperature was controlled to stir at 5-10 C, filtered, and the filter cake was rinsed with 100 mL of water.drying. The crude product was beaten with 50 mL of n-hexane for 20 min and filtered.The filter cake was dried to give 4.9 g of a yellow solid. Yield: 80.19%.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Beijing Purunao Bio-technology Co., Ltd.; Zhang Peilong; Shi Hepeng; Lan Wenli; Song Zhitao; (250 pag.)CN108707139; (2018); A;,
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Related Products of 53087-13-1, 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. 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 1-benzyloxy-2-bromobenzene (12.8 g, 48.7 mmol) and n-butyllithium (55 mmol) in THF (150 mL) was stirred for 20 min at -78 C, treated with tri-iso-propyl borate (34 mL, 147 mmol), stirred for 20 minutes at -78 C, then 30 minutes at ambient temperature. The mixture was reduced in volume by rotary evaporation, diluted with ethyl acetate washed sequentially with 1M HCl (twice), water, and brine, dried (MgSO4) and concentrated to provide a white solid which was triturated with hexanes to provide the title compound as a white powder (7.04 g). MS (DCI/NH3) m/e 246 (M+NH4)+.

The chemical industry reduces the impact on the environment during synthesis 1-(Benzyloxy)-3-bromobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ABBOTT LABORATORIES; EP1080070; (2006); B1;,
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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. 59557-91-4, name is 4-Bromo-2-methoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C7H8BrNO

To a round bottom flask at r.t. containing formic acid (85%, 27 mL, 624.4 mmol) was added acetic anhydride (16 mL, 169.5 mmol) dropwise. The reaction stirred for 45 min. followed by the dropwise addition of a solution of 4-bromo-2- methoxyaniline (9.01 g, 44.6 mmol) in THF (56 mL). The reaction mixture was quenched with ice-water after 23 h and the resulting precipitate was filtered to afford compound 74a (9.20 g, 90%) as a brown solid. 1HNMR (CDCI3, 400 MHz) 8.45 (d, 1H), 8.26 (d, 1H), 7.72 (s, 1H)1 7.11-7.01 (m, 2H), 3.89 (s, 3H); MS (M-NHCOH+1)+ m/z calcd for C7H6BrO+ = 187.0, found m/z = 187.1

The synthetic route of 59557-91-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; WO2009/73777; (2009); A1;,
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Reference of 75148-49-1,Some common heterocyclic compound, 75148-49-1, name is 3-Bromobenzaldehyde Diethyl Acetal, molecular formula is C11H15BrO2, 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.

Step 2. 3-iodobenzaldehyde diethyl acetal. To a stirred -78 C. solution of 3-bromobenzaldehyde diethyl acetal, prepared as in step 1, (1.0 g, 3.8 mmol) in THF (10 mL) was added n-butyllithium (1.7 mL, 4.25 mmol, 2.5M in hexanes). The cold reaction mixture was stirred 0.5 hours followed by the addition of a THF (5 mL) solution of iodine (1.09 g, 4.25 mmol). The ice bath was removed and the reaction allowed to warm to ambient temperature. Saturated NH4 Cl was added and the mixture diluted with hexanes. The organic layer was washed with brine, dried (MgSO4) and concentrated under reduced pressure to give a residue which was purified by column chromatography on silica gel eluding with 5% ethyl acetate-hexanes to afford 1.0 g of 3-iodobenzaldehyde diethyl acetal.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromobenzaldehyde Diethyl Acetal, its application will become more common.

Reference:
Patent; Abbott Laboratories; US5616596; (1997); A;,
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