p-Toluidine → HCID 21106134, compound

Participants

Reaction Steps

An oven-dried resealable schlenk tube containing a stir bar was charged with Pd2(dba)3 (4.6 mg, 0.005 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (19.0 mg, 0.04 mmol), 2-bromoacetanilide (107 mg, 0.5 mmol), p-toluidine (80 mg, 0.75 mmol) and K3PO4 (265 mg, 1.25 mmol). The tube was capped with a rubber septum, evacuated and backfilled with argon. tbutanol (1 mL) was added through the septum via syringe. The septum was replaced with a Teflon screw cap. The schlenk tube was sealed and put into a pre-heated oil bath at 110° C. The reaction mixture was stirred for 18 h, allowed to cool down to room temperature and filtered through celite with ethyl acetate. The filtrate was concentrated under reduced pressure. Chromatography on silica gel column with 1:1 hexane:ethyl acetate gave 107 mg (89%) of the title compound as a brown solid.

Provenance & Evidence