Acetic Acid → (5-Bromo-2-fluorophenyl)boronic acid

Temperature

-78 °C

A solution of 2,4-dibromofluorobenzene (12.7 g, containing 30% 3,4-dibromofluorobenzene) in dry tetrahydrofuran (THF) (10 ml) is added over 5 min to a stirred suspension of magnesium turnings (1.15 g) in dry THF (50 ml) under an atmosphere of nitrogen and cooled in a water bath. After 1 hour, when all the magnesium has reacted, this reagent is added over 20 min to a stirred solution of trimethoxyborane (7 ml) in dry diethyl ether (80 ml) under an atmosphere of nitrogen and cooled at -78° C. The mixture is stirred at -78° C. for a further 15 min. and glacial acetic acid (6 ml) added followed by water (50 ml). The mixture is warmed to room temperature, extracted with diethyl ether (×3), washed with water, dried and the solvent evaporated under reduced pressure. The residue is stirred with carbon tetrachloride (30 ml) and then cooled at 0° C. The crystals of dihydroxy-(5-bromo-2-fluorophenyl)-borane are filtered off and washed with a little carbon tetrachloride. Yield 2.8 g m.p.t. 173°-174° C.

1. temperaturecooled in a water bath
2. temperatureThe mixture is warmed to room temperature
3. extractionextracted with diethyl ether (×3)
4. washwashed with water
5. customdried
6. customthe solvent evaporated under reduced pressure
7. stirringThe residue is stirred with carbon tetrachloride (30 ml)
8. temperaturecooled at 0° C
9. filtrationThe crystals of dihydroxy-(5-bromo-2-fluorophenyl)-borane are filtered off
10. washwashed with a little carbon tetrachloride
11. custom173°-174° C.

ORD record

ord-f13aaabea388456cb9de04bc910f8f16

Source dataset

uspto-grants-1994_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05283371