1-(3-Bromophenyl)propan-2-one → 1-(3-Bromophenyl)-2-methylpropan-2-ol

Temperature

0 °C

Methylmagnesium bromide (3M solution in diethyl ether, 51.6 mL, 155 mmol) was slowly added to a solution of 1-(3-bromo-phenyl)propan-2-one (15.0 g, 70 mmol) in dry diethyl ether (200 mL) at 0° C. and the mixture was stirred for 3 hours. The reaction mixture was then re-cooled to 0° C. and slowly quenched with saturated aqueous ammonium chloride solution. The organic solution was washed with brine, dried over sodium sulfate and concentrated in vacuo. The residual yellow oil was then purified by column chromatography on silica gel eluting with dichloromethane:pentane:methanol, 90:5:5, to afford a pale yellow oil in 83% yield, 13.26 g. 1H NMR (400 MHz, CDCl3) δ: 1.22 (6H, s), 1.42 (1H, bs), 2.74 (2H, s), 7.15 (2H, m), 7.40 (2H, m)

1. customslowly quenched with saturated aqueous ammonium chloride solution
2. washThe organic solution was washed with brine
3. dry with materialdried over sodium sulfate
4. concentrationconcentrated in vacuo
5. customThe residual yellow oil was then purified by column chromatography on silica gel eluting with dichloromethane
6. custompentane:methanol, 90:5:5, to afford a pale yellow oil in 83% yield, 13.26 g

ORD record

ord-8361ee563a5448d184fb696c89ac8759

Source dataset

uspto-grants-2007_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07241810B2