Pyridine → HCID 68542521, compound

Participants

Reaction Steps

Dissolve 4-bromo-phenyl acetic acid (5 g, 23.3 mmol) in 125 mL dichloromethane. Add 1 mL DMF, stir to give a clear solution, then add oxalyl chloride (3.25 g, 2.23 mL, 25.5 mmol) portionwise via syringe and stir at room temperature for 15-30 minutes until gas evolution ceases. Remove volatiles on rotovap to yield a clear yellow oil. Dissolve the oil in 100 mL amylene-stabilized chloroform, chill on ice and fit flask with a dropping funnel. Fill the dropping funnel with a solution of 4-amino-2-trifluoromethyl-benzonitrile (4.65 g, 25 mmol) and pyridine (6.05 g, 6.19 mL, 76.5 mmol) in 200 mL amylene-stabilized chloroform. Add the benzonitrile solution to the cold acid chloride solution with stirring over 30 minutes, remove the ice bath and stir overnight at room temperature. Dilute the reaction mixture with 200 mL dichloromethane, wash twice with 250 mL portions of 1 N NaHSO4, once with aqueous saturated sodium chloride, then dry over MgSO4 and concentrate to a brown solid. Purify on Biotage 75L® silica cartridge in 4.5:4.5:1 CH2Cl2:hexanes:diethyl ether to yield 4.33 g (48%) of the title compound as a pale yellow-ivory solid. LCMS (ES) m/z 381,383 (M−1).

Provenance & Evidence