Hexane → 4-Borono-3-methylbenzoic acid

Participants

Reaction Conditions

Reaction Steps

A stirred solution of 4-bromo-3-methylbenzoic acid (5.0 g, 0.020 mole) in dry THF (250 ml) at -78° C. under argon was treated with 1.6M n-butyllithium in hexane (36 ml, 0.057 mole). After 15 minutes, the reaction mixture was treated with triisopropylborate (13.4 ml, 0.050 mole), then stirred at -78° C. for 1 h, followed by room temp. for 19 h. The mixture was treated with water (25 ml), then concentrated in vacuo and the residue chromatographed on silica gel eluting with 10% methanol/dichloromethane to afford the title compound as a white solid (2.63 g, 67%).

Provenance & Evidence