3-Bromo-6-methoxy-2-methylbenzonitrile → 3-Acetyl-6-methoxy-2-methylbenzonitrile

Participants

Reaction Conditions

Reaction Steps

To a 20 mL microwave tube was added a stir bar, 3-bromo-6-methoxy-2-methylbenzonitrile (4.0 g, 18 mmol), vinyl ethoxy tributyltin (9.5 g, 26 mmol), palladium tetrakis (1.0 g, 0.88 mmol), and anhydrous toluene (15 mL). The tube was capped, degassed and purged with N2. The reaction mixture was heated to 110° C. for 12 hours. The tube was cooled to room temperature and treated with 4 M HCl (10 mL) and stirred for 1 hour. The crude product was extracted with EtOAc. The extraction was washed with brine, dried with Na2SO4, filtered and concentrated in vacuo. The crude residue was purified by silica gel column chromatography (Hexanes:EtOAc=1:1) to afford the title product.

Provenance & Evidence