Trimethyl borate → 4-(2-Hydroxy-2-methylpropoxy)phenylboronic acid

Temperature

-78 °C

A solution of 1-(4-bromophenoxy)-2-methylpropan-2-ol (1.23 g) in tetrahydrofuran (25 ml) was added to oil-free sodium hydride (132 mg) under an atmosphere of argon. The mixture was stirred for 30 minutes and then cooled to -78° C. 1.6M Butyl lithium in hexane (6.9 ml) was added over 5 minutes and the solution was stirred at -78° C. for 30 minutes. Trimethylborate (1.14 g) was added over 1 minute and the mixture was stirred at -78° C. for 1 hour. Saturated ammonium chloride solution (25 ml) was added and the mixture was allowed to warm to room temperature. Water (25 ml) was added and the mixture was extracted with ether (2×25 ml). The extracts were washed with water (25 ml) and saturated sodium chloride solution (25 ml) and dried (MgSO4). Volatile material was removed by evaporation and the residue was purified by flash chromatography, eluting with ethyl acetate/hexane (7:3 v/v), to give 4-(2-hydroxy-2-methylpropoxy)phenylboronic acid (355 mg), 1H NMR (d6 -DMSO): 1.2 (s, 6H), 3.7 (s, 2H), 4.5 (br s, 1H), 6.85 (d, 2H), 7.6-7.8 (m, 4H

1. stirringthe solution was stirred at -78° C. for 30 minutes
2. stirringthe mixture was stirred at -78° C. for 1 hour
3. temperatureto warm to room temperature
4. extractionthe mixture was extracted with ether (2×25 ml)
5. washThe extracts were washed with water (25 ml) and saturated sodium chloride solution (25 ml)
6. dry with materialdried (MgSO4)
7. customVolatile material was removed by evaporation
8. customthe residue was purified by flash chromatography
9. washeluting with ethyl acetate/hexane (7:3 v/v)

ORD record

ord-b8d45346fa87446d97365cebc07ad6c9

Source dataset

uspto-grants-2000_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06060475