Potassium Carbonate → 4-(4-Butyl-phenylamino)-benzamide

Participants

Reaction Conditions

Reaction Steps

An oven-dried resealable Schlenk flask was evacuated and backfilled with argon. The flask was charged with Pd2(dba)3 (4.6 mg, 0.005 mmol, 1 mol % Pd), Ligand 1 (9.4 mg, 0.02 mmol, 2 mol %), ground K2CO3 (193 mg, 1.4 mmol), and 4-amino-benzamide (163 mg, 1.2 mmol). The flask was evacuated and backfilled with argon (3×) and then capped with a rubber septum. To the flask was added t-BuOH (1.5 mL), 4-n-butyl-chlorobenzene (168 mg, 1.0 mmol) and t-BuOH (0.5 mL). The septum was replaced with a Teflon screwcap, the flask was sealed, and the mixture was heated to 110° C. with stirring until the starting aryl chloride was consumed by GC analysis (19 h). The reaction was cooled to room temperature, diluted with ethyl acetate, filtered through Celite, and concentrated under reduced pressure. The crude material was purified by column chromatography on silica gel (eluting with EtOAc/hexanes, 8:2) to give the desired product as a white solid (235 mg, 88%).

Provenance & Evidence