Category: 906673-45-8

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. 906673-45-8, name is 4-(4-Bromo-3-(hydroxymethyl)phenoxy)benzonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 906673-45-8

Compound IV (1.00 g, 3.3 mmol, 1.0 eq) was dissolved in DMF (15 mL), 60% sodium hydride (0.16 g, 4.0 mmol, 1.2 eq) was added, and stirred at room temperature for 30 min. 2,3,4-Trimethoxybenzyl chloride (1.00 g, 4.6 mmol, 1.4 eq) was added, and the reaction was stirred by heating to 85 C. After 6h, TLC showed that the basic reaction of the raw materials was completed, post-processing was carried out, and the reaction solution was cooled to room temperature. The reaction mixture was quenched by adding 20 mL of water, extracted with 50 mL EA, liquid separation was carried out, the organic phase was washed, dried, concentrated and the crude product was purified by column chromatography to give 1.46 g of yellow oil. That is, the target compound, the yield was 76%.

The synthetic route of 906673-45-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Suzhou Wangshanwangshui Bio-pharmaceutical Co., Ltd.; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute Suzhou Pharmaceutical Chuangxin Institute; Shandong Tefaman Pharmaceutical Co., Ltd.; Tian Guanghui; Wu Jianzhong; Yu Jianghui; Pang Zhenqiang; Li Junyong; (10 pag.)CN108047261; (2018); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

These common heterocyclic compound, 906673-45-8, name is 4-(4-Bromo-3-(hydroxymethyl)phenoxy)benzonitrile, 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. name: 4-(4-Bromo-3-(hydroxymethyl)phenoxy)benzonitrile

To a solution of 40g (0.13 mole) of 4-(4-bromo-3-(hydroxymethyl) phenoxy) benzonitrile (V) and 20.21 g (0.198 mol) of acetic anhydride in dichloromethane, two drops of pyridine was added, and the mixture was stirred at room temperature. After completion of reaction, the reaction mixture was quenched with water and extracted with dichloromethane. The organiclayer was separated, washed with saturated sodium bicarbonate solution 0. iN hydrochloric acid and water and dried over sodium sulphate. On filtration, the filtrate was evaporated to remove the solvent completely and yield 2-bromo-5-(4-cyanophenoxy) benzyl acetate (IV).Yield %: 97.0; Purity %: 98.0

The synthetic route of 4-(4-Bromo-3-(hydroxymethyl)phenoxy)benzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOPHORE INDIA PHARMACEUTICALS PVT. LTD.; PULLAGURLA, Manik Reddy; PITTA, Bhaskar Reddy; NAMANA, Suresh Babu; RANGISETTY, Jagadeesh Babu; (21 pag.)WO2018/207216; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 906673-45-8,Some common heterocyclic compound, 906673-45-8, name is 4-(4-Bromo-3-(hydroxymethyl)phenoxy)benzonitrile, molecular formula is C14H10BrNO2, 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.

40.0 g (131 mmol) of 4-(4-bromo-3-hydroxymethyl-phenoxy)-benzonitrile of formula (II), prepared as described in Example 3, are added under nitrogen to 400 mL THF and 23.8 g (236 mmol) of triethylamine in a previously anhydrified flask. The solution is cooled down to 0 C. and 16.9 g (157 mmol) of trimethylsilyl chloride are added maintaining the temperature below 15 C. After completion of the addition, the mixture is allowed to reach room temperature. 50 mL of toluene and 100 mL of water are added and the phases are separated. The organic phase is washed with a saturated NaCl solution and evaporated to dryness under reduced pressure to obtain 49.4 g of 4-(4-bromo-3-trimethylsilanoxymethyl)-benzonitrile of formula (II) as a solid with a yield of 98%. The obtained product is used in the next step any without further purification. 1H-NMR (CDCl3, 300 MHz) delta (ppm): 7.63-7.60 (2H, m) 7.52 (1H, d, J=8.4 Hz), 7.22 (1H, m) 7.03-7.00 (2H), 6.85-6.80 (1H, m) 4.69 (2H, s), 0.17 (9H, s)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(4-Bromo-3-(hydroxymethyl)phenoxy)benzonitrile, its application will become more common.

Reference:
Patent; DIPHARMA FRANCIS S.R.L.; Santillo, Niccolo’; Attolino, Emanuele; Brenna, Davide; Vladiskovic, Chiara; Lombardo, Alessandro; Razzetti, Gabriele; US2019/241585; (2019); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 906673-45-8, These common heterocyclic compound, 906673-45-8, name is 4-(4-Bromo-3-(hydroxymethyl)phenoxy)benzonitrile, 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.

Compound IV (5.00 g, 16.4 mmol, 1.0 eq) and DHP (2.07 g, 24.6 mmol, 1.5 eq) was dissolved in dichloromethane (40 mL). p-Toluenesulfonic acid (0.28 g, 1.6 mmol, 0.1 eq) was added, and the reaction mixture was stirred. After 5h, TLC showed that the basic reaction of the raw materials was completed, post-processing was carried out, the reaction mixture was quenched by the addition of 50 mL of aqueous sodium hydrogencarbonate solution, extracted with 50 mL of dichloromethane, liquid separation was carried out, the organic phase was washed, dried, concentrated, and the obtained crude product was purified by column chromatography to yield 5.71 g of a yellow oil in a yield of 89%.

The synthetic route of 906673-45-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Suzhou Wangshanwangshui Bio-pharmaceutical Co., Ltd.; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute Suzhou Pharmaceutical Chuangxin Institute; Shandong Tefaman Pharmaceutical Co., Ltd.; Tian Guanghui; Wu Jianzhong; Yu Jianghui; Pang Zhenqiang; Li Junyong; (10 pag.)CN108047261; (2018); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 906673-45-8, A common heterocyclic compound, 906673-45-8, name is 4-(4-Bromo-3-(hydroxymethyl)phenoxy)benzonitrile, molecular formula is C14H10BrNO2, 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.

In a three-necked flask, compound II (1.9 g), tetrahydrofuran (57 mL), triisopropyl borate (1.53 g) were added to cool down to -78C, and butyllithium (6.25 mL, 2.5 M concentration) was added dropwise.After completion of the reaction for 30 minutes or more, after completion of the reaction, 1N hydrochloric acid (57 mL) was added to quench the reaction, stirred for 30 minutes or more, and allowed to stand for stratification.The organic phase was concentrated under reduced pressure until no solvent was evaporated. Methanol (20 mL) was added to the obtained oil, concentrated hydrochloric acid (0.5 mL) was stirred at room temperature overnight, and after completion of the reaction, the mixture was concentrated under reduced pressure to obtain the target compound I (about 1.8 g).

The synthetic route of 906673-45-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Yaoyuan Pharmaceutical Chemical (Shanghai) Co., Ltd.; Wang Yuan; Liu Chuanjun; Tang Wensheng; He Xungui; (8 pag.)CN107759625; (2018); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 906673-45-8,Some common heterocyclic compound, 906673-45-8, name is 4-(4-Bromo-3-(hydroxymethyl)phenoxy)benzonitrile, molecular formula is C14H10BrNO2, 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.

In a three-necked flask, Compound II (20 g) was added, tetrahydrofuran (600 mL), trimethyl borate (14 g) was cooled to -78C, and butyllithium (64 mL, 2.5 M concentration) was added dropwise.The reaction was completed for 30 minutes or more. After the reaction was completed, 1N hydrochloric acid (600 mL) was added to quench the reaction, stirred for 30 minutes or longer, and allowed to stand for stratification.The organic phase was concentrated to dryness under reduced pressure, methanol (200 mL) was added to the resulting oil, concentrated hydrochloric acid (5 mL), and the mixture was stirred overnight at room temperature. After completion of the reaction, the mixture was concentrated under reduced pressure to give about 17 g of the target compound I.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(4-Bromo-3-(hydroxymethyl)phenoxy)benzonitrile, its application will become more common.

Reference:
Patent; Yaoyuan Pharmaceutical Chemical (Shanghai) Co., Ltd.; Wang Yuan; Liu Chuanjun; Tang Wensheng; He Xungui; (8 pag.)CN107759625; (2018); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

906673-45-8, name is 4-(4-Bromo-3-(hydroxymethyl)phenoxy)benzonitrile, belongs to nitriles-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. Application In Synthesis of 4-(4-Bromo-3-(hydroxymethyl)phenoxy)benzonitrile

30.2 g (0.1 mol) of 4-[(4-bromo-3-hydroxymethyl)phenoxy)]benzonitrile, 300 ml of dichloromethane, and 30.3 g of triethylamine (0.3 mol) were added to the reaction kettle. The reaction was cooled to 0-10 C, 12.96 g of trimethylchlorosilane was added dropwise, the temperature was controlled to not exceed 10 C, stirred at 25 C for 24 h, quenched with water, extracted with dichloromethane, washed with water and dried over anhydrous magnesium sulfate, filtered, and the solvent was recovered to give an oil (31.8 g) , yield 85%;

The synthetic route of 906673-45-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wuhan Polytechnic University; Zhao Ling; Yang Bo; (8 pag.)CN108659024; (2018); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 906673-45-8, name is 4-(4-Bromo-3-(hydroxymethyl)phenoxy)benzonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 4-(4-Bromo-3-(hydroxymethyl)phenoxy)benzonitrile

4-(4-bromo-3-(hydroxymethyl)phenoxy)benzonitrile (compound B) (10.0 g, 32.9 mmol), potassium acetate (9.7 g, 99.0 mmol), XPhos (0.078 g, 0.16 mmol), XPhos-Pd-G2 (0.068 g, 0.082 mmol) and tetrahydroxydiboron (4.4 g, 49.3 mmol) were added to an oven dried glass reactor with a positive N2 pressure. The vessel was sealed and then evacuated and backfilled with N2 (four times). MeOH (100 mL, degassed) was added via syringe, followed by the addition of ethylene glycol (5.5 mL, 99.0 mmol). The reaction was then heated to 64-66 C until the starting material was consumed (as monitored by TLC). The solvent was concentrated in vacuo and the crude reaction product was dissolved in EtOAc (50 mL) and then transferred to a separatory funnel. H20 was added (50 mL), the layers were separated and the aqueous layer was further extracted with more EtOAc (30 mL). The combined organic layers were washed once with 1 M HCI (30 mL) and once with H20 (30 mL), then dried over Na2S04 and concentrated in vacuo. The solid residue was purified twice by recrystallization in hot methanol, thus affording pure 4-[(1-hydroxy-1 ,3-dihydro- 2,1-benzoxaborol-5-yl)oxy]benzonitrile (crisaborole) (6.6 g, 26.3 mmol) as a white solid. Yield: 80% (calculated from 4-(4-bromo-3-(hydroxymethyl)phenoxy)benzonitrile) Purity by HPLC: > 99.9% 1H-NMR (200 MHz, DMSO-d6, delta ppm): 9.22 (1 H, s); 7.85-7.83 (2H, m, J= 8.9 Hz); 7.81 -7.79 (1 H, d, J= 8.1 Hz); 7.15-7.13 (3H, m); 7.10-7.08 (1 H, dd, J= 8.1 , 2.1 Hz); 4.97 (2H, s) 13C-NMR (50 MHz, DMSO-d6, ppm): 160.6; 157.1 ; 156.6; 134.7; 132.6; 1 18.9; 1 18.6; 1 12.7; 105.5; 69.7.] FT-IR: 2222.9, 1600.8, 1501.2, 1467.5, 1406.0, 1390.9, 1360.6, 1244.7, 1 167.3, 1 1 16.1 , 1010.7, 937.3, 892.5

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; LABORATORIOS LESVI, SL; HUGUET CLOTET, Juan; OZORES VITURRO, Lidia; RODRIGUEZ ROPERO, Sergio; DALMASES BARJOAN, Pere; (39 pag.)WO2018/115362; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts