4-Bromoanisole → (4-Methoxyphenyl)boronic acid

Participants

Reaction Steps

To a solution of 4-bromoanisole (100 g, 0.53 mol) in dry THF (1 L), BuLi (494 ml-, 0.64 mol) was added slowly at −78° C. and stirred for 2 h. To this was added n-butylborate (147 g, 0.64 mol) slowly over 30 min and stirred at RT for 12 h. After completion, the reaction mixture was quenched with water (400 ml), acidified with 1.5N HCl and filtered off the solid precipitate. The solid was washed with water and dried to give 4-methoxyphenylboronic acid (75 g, 92%).

Provenance & Evidence