Category: 867366-91-4

Application of 867366-91-4, A common heterocyclic compound, 867366-91-4, name is 3-Bromo-5-methoxybenzonitrile, molecular formula is C8H6BrNO, 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.

Example 43 2-[(4-Fluoro-benzenesulfonyl)-methyl-amino]-N-(5-methoxy-4′-trifluoromethyl-biphenyl-3- ylmethyl)-acetamide A solution of 4,4,5,5-tetramethyl-2-(4-trifluoromethyl-phenyl)-[l,3,2]dioxaborolane(1.00 g, 3.68 mmol), 3-bromo-5-methoxy-benzonitrile (0.78 g, 3.68 mmol) and potassium carbonate (0.51 g, 3.68 mmol) in DMF (5 mL) at 25C was purged with nitrogen gas and evacuated three times. The solution was then treated with teira 3s(triphenylphosphine)palladium(0) (212 mg, 184 muiotaetaomicron) and then sealed and heated to 120C for 14 h. The reaction mixture was cooled to 25 C, unsealed and poured into water. The aqueous phase was extracted three times with ethyl acetate. The combined organic layers were washed with brine and dried over magnesium sulfate. Filtration followed by concentration in vacuo gave a brown solid. Flash chromatography (80/20 hexanes/ethyl acetate) afforded 5-methoxy- 4′-trifluoromethyl-biphenyl-3-carbonitrile (0.70 g, 69%) as a white solid.

The synthetic route of 867366-91-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BROTHERTON-PLEISS, Christine E.; CHEN, Huifen; CHEN, Shaoqing; CHEN, Zhi; ERICKSON, Shawn David; ESTRADA, Anthony; KIM, Kyungjin; LI, Hongju; LOVEY, Allen John; LYSSIKATOS, Joseph P.; QIAN, Yimin; SO, Sung-Sau; WOVKULICH, Peter Michael; YI, Lin; WO2014/49047; (2014); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 867366-91-4, 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. 867366-91-4, name is 3-Bromo-5-methoxybenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

3-bromo-5- methoxybenzonitrile (8.3 g, 39.1 mmol),dicyclohexyl(2′,6′-dimethoxy-[l, -biphenyl]-2- yl)phosphine (S-Phos) (1.286 g, 3.13 mmol), phenylboronic acid (5.84 g, 47.0 mmol), Pd2(dba)3 and 200 mL toluene were charged in a flask and refluxed overnight. The reaction was cooled down and 200 mL of ethyl acetate was added. The crude mixture was run though a silica gel plug, and the product was confirmed by GC. After distillation under vacuum, 7.5 g of a white product was obtained.

The chemical industry reduces the impact on the environment during synthesis 3-Bromo-5-methoxybenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; UNIVERSAL DISPLAY CORPORATION; XIA, Chuanjin; YEAGER, Walter; LI, David Zenan; FIORDELISIO, James; MA, Bin; ELSHENAWY, Zeinab; LAYEK, Suman; BARRON, Edward; KOTTAS, Gregg; BROOKS, Jason; WO2012/116231; (2012); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 867366-91-4, name is 3-Bromo-5-methoxybenzonitrile, belongs to nitriles-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 867366-91-4, SDS of cas: 867366-91-4

Step 2 A solution of 3-bromo-5-methoxybenzaldehyde (4.02 g, 18.7 mmol) and hydroxylamine hydrochloride (6.50 g, 93.5 mmol) in pyridine (50 ML) and EtOH (50 ML) was heated to 65 C. for 16 h.The solvent was removed, and the remaining materials were partitioned between 1:1 EtOAc/hexanes (150 ML) and H2O (75 ML).The organic layer was washed with brine (60 ML), and the solvents were evaporated.The remaining oil was dissolved in anhydrous dioxane (50 ML), and trifluoroacetic anhydride (5.1 ML, 37.4 mmol) and pyridine (9.07 ML, 112.2 mmol) were added.The mixture was heated to 60 C. for 3 h and then cooled to RT. CHCl3 (100 ML) was added, and the organic layer was washed with H2O (2*50 ML), 5% aqueous HCl solution (30 ML), brine (30 ML), and dried with anhydrous MgSO4.The solvents were removed to provide a white solid.This solid was placed in a 150 ML flask that was flushed with nitrogen.Collidine (40 ML) and LiI (7.92 g, 59.10 mmol) were added, and the mixture was heated to 180 C. for 5 h.The reaction mixture was cooled to RT, and partitioned between H2O (400 ML) and EtOAc (100 ML).The layers were separated, and the aqueous layer was acidified with 10% aqueous HCl solution, and extracted with 2:1 EtOAc/hexanes (3*125 ML).The combined organic layers were washed with H2O (100 ML), 10% aqueous HCl solution (2*50 ML), brine (75 ML), and dried with anhydrous MgSO4.The solvents were evaporated and the resulting solid was purified by flash chromatography on silica gel (10% to 40% EtOAc/hexanes) to provide 3.40 g (92%) of 3-bromo-5-hydroxybenzonitrile (116)116).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromo-5-methoxybenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Roche Palo Alto LLC; US2004/198736; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts