Methanol → 4-Methoxycarbonylphenylboronic acid

A solution of 4-carboxyphenylboronic acid (25 g) and concentrated sulphuric acid (1 ml) in methanol (250 ml) was heated under reflux for 36 hours. Volatile material was removed by evaporation and the residue was dissolved in ethyl acetate (200 ml). Water (100 ml) was added and the mixture was stirred for 1 hour. The organic phase was separated and washed with saturated sodium bicarbonate solution (50 ml), water (100 ml) and saturated sodium chloride solution (50 ml). The solution was dried (MgSO4) and the solvent was removed by evaporation to give 4-methoxycarbonylphenylboronic acid (27.7 g), m.p. 227-229° C.

1. temperatureunder reflux for 36 hours
2. customVolatile material was removed by evaporation
3. dissolutionthe residue was dissolved in ethyl acetate (200 ml)
4. additionWater (100 ml) was added
5. customThe organic phase was separated
6. washwashed with saturated sodium bicarbonate solution (50 ml), water (100 ml) and saturated sodium chloride solution (50 ml)
7. dry with materialThe solution was dried (MgSO4)
8. customthe solvent was removed by evaporation

ORD record

ord-720b1e8e5ee94f779c90bba05487a618

Source dataset

uspto-grants-2001_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06258817B1