Nitric Acid → 3-Bromo-4-methoxyphenylacetonitrile

Participants

Reaction Steps

To a mixture of compound 4-methoxyphenyl acetonitrile (5.88 g, 40 mmol), KBr (9.52 g, 80 mmol), tetrabutylammonium chloride (332 mg, 1.2 mmol) in dichloroethane (80 mL), was added 21% w/w nitric acid (48 g, 160 mmol). The reaction mixture was stirred at rt for 20 h, diluted with dichloromethane (80 mL) and washed with sat. NaHCO3 aq. (2×50 mL), water (2×50 mL), brine and dried over Na2SO4. After removal of solvent under vacuum, the residue was triturated with Et2O (10 ml)/hexanes (40 ml) to give 6.32 g of product; Yield: 70%.

Provenance & Evidence