Hexane → 4-Borono-3-methylbenzoic acid

Participants

Reaction Conditions

Reaction Steps

A stirred solution of 4-bromo-3-methylbenzoic acid (5.0 g, 0.02 mole) in dry THF (250 ml) at -78° C. under argon was treated with 1.6M n-butyllithium in hexane (36.3 ml, 0.05 mole). The mixture changed from a clear solution to an orange suspension. This was stirred at -78° C. for 0.25 h, then treated with triisopropyl borate (13.4 ml, 0.05 mole) and stirred at -78° C. for a further 1 h. The mixture was allowed to warm to room temp. and stirred for 19 h, then treated with water (25 ml) and concentrated in vacuo. The residue was chromatographed on silica gel eluting with 10% methanol/dichloromethane to afford the title compound as a white solid (2.63 g, 67%).

Provenance & Evidence