Category: ethers-buliding-blocks

Some common heterocyclic compound, 156573-09-0, name is 1-Bromo-4-ethoxy-2,3-difluorobenzene, molecular formula is C8H7BrF2O, 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. HPLC of Formula: C8H7BrF2O

First Step THF (100 ml) was added to 1-bromo-4-ethoxy-2,3-difluorobenzene (5.1 g) in a reaction vessel under an atmosphere of nitrogen, and the mixture was cooled to -78 C. n-Butyllithium (1.57 M, in a hexane solution) (13.8 ml) was added dropwise at a temperature of -70 C. or lower. The stirring was continued at -78 C. for another 2 hours, and 4-(3-propylcyclopentyl)-cyclohexanone (3.0 g) in a THF (10 ml) solution was added dropwise at a temperature of -70 C. or lower. After the mixture had been stirred at -78 C. for another 1 hour, it was warmed to room temperature, and a saturated aqueous solution of ammonium chloride (50 ml) was added. The mixture was separated, and the water layer was extracted with ethyl acetate three times, and then the combined organic layer was washed with brine. The solution was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluent: ethyl acetate/n-heptane= 1/9 by volume) to give 1-(4-ethoxy-2,3-difluorophenyl)-4-(3-propylcyclopentyl)cyclohexanol (5.0 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 156573-09-0, its application will become more common.

Reference:
Patent; CHISSO PETROCHEMICAL CORPORATION; JNC CORPORATION; US2011/309300; (2011); A1;,
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Related Products of 54314-84-0, 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. 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Into a 500-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 210.2 (9.9 g, 34.82 mmol, 1.00 equiv), N,N-dimethylformamide (200 mL). This was followed by the addition of NaH (1.25 g, 52.08 mmol, 1.50 equiv) at 0° C. in a water/ice bath. The mixture was stirred for 1 h at 0° C. To this was added [(3-bromopropoxy) methyl] benzene (11.92 g, 52.03 mmol, 1.50 equiv). The resulting solution was stirred overnight at room temperature. The reaction was then quenched by the addition of 200 mL of NH4Cl (aq). The resulting solution was extracted with 2×300 mL of ethyl acetate and the organic layers combined and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:15). This resulted in 3.3 g (22percent) of 210.3 as yellow oil.

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, ((3-Bromopropoxy)methyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Gilead Apollo, LLC; Ghosh, Shomir; Greenwood, Jeremy Robert; Harriman, Geraldine C.; Leit De Moradei, Silvana Marcel; (290 pag.)US2017/166584; (2017); A1;,
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Synthetic Route of 349-65-5, 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 349-65-5 as follows.

To a stirring solution of phosgene (1.9 M in toluene; 2.07 mL 0.21 g, 1.30 mmol) in CH2Cl2 (20 mL) at 0 C. was added anh pyridine (0.32 mL) followed by 2-methoxy-5-(trifluoromethyl)aniline (0.75 g). The yellow solution was allowed to warm to room temp during which a precipitate formed. The yellow mixture was stirred for 1 h, then concentrated under reduced pressure. The resulting solids were treated with anh toluene (20 mL) followed by 4-(2-(N-methylcarbamoyl)-4-pyridyloxy)aniline (prepared as described in Method A2; 0.30 g) and the resulting suspension was heated at 80 C. for 20 h, then allowed to cool to room temp. The resulting mixture was diluted with water (100 mL), then was made basic with a saturated NaHCO3 solution (2-3 mL). The basic solution was extracted with EtOAc (2×250 mL). The organic layers were separately washed with a saturated NaCl solution, combined, dried (MgSO4), and concentrated under reduced pressure. The resulting pink-brown residue was dissolved in MeOH and absorbed onto SiO2 (100 g). Column chromatography (300 g SiO2; gradient from 1% Et3N/33% EtOAc/66% hexane to 1% Et3N/99% EtOAc to 1% Et3N/20% MeOH/79% EtOAc) followed by concentration under reduced pressure at 45 C. gave a warm concentrated EtOAc solution, which was treated with hexane (10 mL) to slowly form crystals of N-(2-methoxy-5-(trifluoromethyl)phenyl)-N’-(4-(2-(N-methylcarbamoyl)-4-pyridyloxy)phenyl) urea (0.44 g): TLC (1% Et3N/99% EtOAc) Rf 0.40.

According to the analysis of related databases, 349-65-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER CORPORATION; US2003/207872; (2003); A1;,
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Synthetic Route of 31804-36-1, These common heterocyclic compound, 31804-36-1, name is 1-Bromo-3-methoxy-2-methylbenzene, 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.

To a solution of intermediate 139 (2.5 g, 12.4 mmol) in THF (30 mL) at -70 C was added n-BuLi (1.6 M in hexane) (7.8 mL, 12.4mmol) dropwise over 5 min by syringe along the wall of the flask. After adding, the reaction was stirred at this temperature for 30 min. Then the resulting solution was added into a solution of (S)-tert-butyl 1,6- dioxohexahydropyrrolo[l,2-a]pyrazine-2(lH)-carboxylate (2.0 g, 12 mmol) in THF (30 mL). After stirred at -70C for 5 min, the reaction mixture was quenched with saturated NH4CI and extracted with EtOAc (2 x 20 mL), washed with brine, dried over Na2S04, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography to give the title compound (2 g, yield : 45 %); m/z (ES+) : 377 [M+H]+.

The synthetic route of 31804-36-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LEO PHARMA A/S; BLADH, Haakon; FELDING, Jakob; ZHOU, Ding; CAI, Zhen-wei; SØRENSEN, Morten Dahl; WO2015/24878; (2015); 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. 54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane, A new synthetic method of this compound is introduced below., Safety of 1-Bromo-2-(2-methoxyethoxy)ethane

Example 1: Synthesis of ironflID /wgyo-tetrakis(N.N-di-(2-(2-methoxyethoxy)ethv?- imidazol-2-vnporphyrin (6) ;(“FeTDPImP”)FeTDPImp (FW: 1626.2 g/mol) was synthesized from a starting imdizaole compound using the following synthetic scheme. The synthetic scheme is shown, along with structures of intermediate products, in FIGS. 2A and 2B.1. Synthesis of N-( 2-(2-methoxyethoxy)ethvI>imidazole (2)Imidazole Ig (0.015 mol) was dissolved in dry DMF 50 mL under argon atmosphere. After a NaH mineral oil dispersion (60%) 0.68g (0.017mol) was added, the mixture was heated at 80 0C for 70 min. After cooling to room temperature, l-Bromo-2- (2-methoxyethoxy)-ethane (1), 2.75 g (0.015 mol), was added, then stirred overnight. The reaction was poured into water, extracted by CHCb, washed by water, dried over Na?SCU, then dried (Rotavap) until an oily residue remained. The crude product was purified with silica gel flash column chromatography with an eluant of CHCh : CH3<_)H=20: 1. 1.69 g(70% yield) of the product (2) was obtained as a colorless oil. As an alternative to column chromatography, product (2) is purified by vacuum distillation

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; TRUSTEES OF PRINCETON; WO2008/45358; (2008); A1;,
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Reference of 5905-69-1,Some common heterocyclic compound, 5905-69-1, name is 1-Bromo-4-(difluoromethoxy)benzene, molecular formula is C7H5BrF2O, 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 3. Synthesis of ethyl 5-(4-(difluoromethoxy)phenyl)isoxazole-3- carboxylate [1.2.11c] 1.2.11c A vial was charged with 1.2.11 b (0.76 g, 1.77 mmol, 1.0 equiv) and 1-bromo-4- uoromethoxy) benzene (0.5 g, 2.13 mmol, 1.2 equiv) were dissolved in 1 ,4-dioxane (10 ml_). Pd(PPh3)2CI2 (0.062 g, 0.085 mmol, 0.05 equiv) was added and the reaction mixture was stirred at 130 C for 2 hours. The reaction mixture was quenched with water and extracted with EtOAc. The organic layer was washed with brine, dried over sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (0-10 % EtOAc in Hexane) to afford product 1.2.11c (0.6 g, 94 % yield). LCMS (m/z): 284.2 [M+H]. 1H NMR (400 MHz, CDCI3) delta 7.89 – 7.81 (m, 2H), 7.28 – 7.24 (m, 2H), 6.93 (s, 1 H), 6.4 – 6.9 (3s, 1 H), 4.19 (q, J = 7.1 Hz, 2H), 1.31 – 1.29 (t, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-4-(difluoromethoxy)benzene, its application will become more common.

Reference:
Patent; NOVARTIS AG; FU, Jiping; KARUR, Subramanian; MADERA, Ann Marie; PECCHI, Sabina; SWEENEY, Zachary Kevin; TJANDRA, Meiliana; YIFRU, Aregahegn; WO2014/160649; (2014); A1;,
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These common heterocyclic compound, 1758-46-9, name is 2-Phenoxyethylamine, 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. Safety of 2-Phenoxyethylamine

[0332] A mixture of 2-phenoxyethan-1-amine (10 mmol, 1.0 equiv), 1H-pyrazole-1-carboxamidine hydrochloride (15 mmol, 1.5 equiv, 1 M) and DIPEA (1.5 equiv) in 1,4-dioxane/H20 (2:1) was refluxed for 8 hours, cooled down to r.t. and evaporated to dryness. Anorange oily residue was treated with water and resulting solution was saturated with solid K2C03 to induce the precipitation of free guanidine. Formed precipitate was filtered off, washed withcold water and dried on a rotary evaporator to afford a title compound. Yield: 0.878 g (49percent).

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

Reference:
Patent; EVERON BIOSCIENCES, INC.; GUDKOV, Andrei; POLINSKY, Alexander; BALAN, Vitaly; CHERNOVA, Olga; HALL, Brandon, M.; KOMAROB, Pavel, G.; KAZYULKIN, Denis, N.; (236 pag.)WO2017/189553; (2017); A1;,
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Reference of 7664-66-6, A common heterocyclic compound, 7664-66-6, name is 4-Isopropoxyaniline, molecular formula is C9H13NO, 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.

To a solution of 1,1′-carbonyldiimidazole (23.3 mg, 0.144 mmol) in DCM (1 mL) was added 4-isopropoxyaniline (21.7 mg, 0.144 mmol). After stirring at 0 C. for 2 h, 1-thieno[2,3-d]pyrimidin-4-yl-piperidin-4-ol (33.7 mg, 0.143 mmol), as prepared in Example 1a, was added and stirred at RT. After 2 h, DMAP (17.6 mg, 0.144 mmol) was added and stirred at 85 C. overnight. The reaction was then cooled to RT, partitioned between DCM (10 mL) and H2O (10 mL). The organic phase was dried over Na2SO4 and concentrated in vacuo. Purification by prep tlc (1:1 Hexane/EtOAc) afforded the title compound as a light green solid (8.4 mg, 14%). 1H NMR (300 MHz, CDCl3) delta 8.7 (br s, 1H), 7.44 (br m, 1H), 7.29 (m, 3H), 6.85 (m, 2H), 6.56 (br s, 1H), 5.09 (m, 1H), 4.48 (heptet, 1H), 4.17 (m, 2H), 3.75 (m, 2H), 2.11 (m, 2H), 1.87 (m, 2H), 1.31 (d, 6H). LC/MS (ESI): calcd mass 412.2, found 413.2 [M+1]+.

The synthetic route of 7664-66-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Baumann, Christian Andrew; Gaul, Michael David; US2006/281769; (2006); A1;,
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Reference of 1663-61-2,Some common heterocyclic compound, 1663-61-2, name is (Triethoxymethyl)benzene, molecular formula is C13H20O3, 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 stirred solution of malononitrile (10mmol, 1.0eq) in acetic anhydride (1.5mL) was added 1,1,1-triethoxypropane and its derivatives (30mmol, 3.0eq). The solution was stirred for 15 h at reflux, cooled, and poured into water. The mixture was extracted with ethyl acetate (200mL), washed with water, brine and dried over sodium sulfate. After concentrated under vacuum, the crude product was purified using silica gel chromatography to give the title compounds. The compounds ware directly used in the next step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (Triethoxymethyl)benzene, its application will become more common.

Reference:
Article; Fang, Zhen; Wang, Tian-qi; Li, Hui; Zhang, Guo; Wu, Xiao-ai; Yang, Li; Peng, Yu-lan; Zou, Jun; Li, Lin-li; Xiang, Rong; Yang, Sheng-yong; Bioorganic and Medicinal Chemistry Letters; vol. 27; 14; (2017); p. 3201 – 3204;,
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Reference of 18800-30-1, The chemical industry reduces the impact on the environment during synthesis 18800-30-1, name is 1-Bromo-4-(2-bromoethoxy)benzene, I believe this compound will play a more active role in future production and life.

1 -Bromo-4-vinyloxybenzene KOf-Bu (14.0 g, 125 mmol) was added in portions over 10 min to a solution of l-bromo-4-(2-bromoethoxy)benzene (19.9 g, 100 mmol see step (a) above) in THF (120 mL) at 0 0C. After 16 h at rt and dilution with water (400 mL), the mixture was extracted with petroleum ether (4×100 mL). The combined extracts were washed with brine, dried (Na2SO4) and concentrated. Vacuum distillation afforded the sub-title compound (11.5 g, 58%).

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-Bromo-4-(2-bromoethoxy)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BIOLIPOX AB; WO2006/77367; (2006); A1;,
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