P-Anisidine → 3-(4-Methoxy-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 dba3 (9.2 mg, 0.01 mmol, 2 mol % Pd), Ligand 1 (19 mg, 0.04 mmol, 4 mol %), K2CO3 (304 mg, 2.2 mmol), 3-chloro-benzamide (156 mg, 1.0 mmol), and 4-methoxy-aniline (148 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 (2.5 mL). The septum was replaced with a Teflon screwcap, the flask was sealed, and the mixture was heated to 100° C. with stirring until the starting aryl chloride was consumed by TLC analysis (20 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, 8.5:1.5) to give the desired product which was re-crystallized from ethyl acetate/hexanes (14/1) to give white flaky crystals (191 mg, 79%).

Provenance & Evidence