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

HRID 494418Notes

Reaction equation

[CH3:1][Mg]Br.[Br:4][C:5]1[CH:6]=[C:7]([CH2:11][C:12](=[O:14])[CH3:13])[CH:8]=[CH:9][CH:10]=1>C(OCC)C>[Br:4][C:5]1[CH:6]=[C:7]([CH2:11][C:12]([CH3:1])([OH:14])[CH3:13])[CH:8]=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Methylmagnesium bromide (3M solution in diethylether, 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 diethylether (200 mL) at 0° C. The resulting mixture was left for 3 hours, then cooled to 0° C. and slowly quenched with saturated aqueous ammonium chloride solution. The organic phase was washed with brine and dried (sodium sulfate). The yellow oil was then purified by column chromatography on silica gel eluting with dichloromethane:pentane:methanol (90:5:5 by volume to afford a pale yellow oil (13.26 g).

Workup

customslowly quenched with saturated aqueous ammonium chloride solution
washThe organic phase was washed with brine
dry with materialdried (sodium sulfate)
customThe yellow oil was then purified by column chromatography on silica gel eluting with dichloromethane:pentane:methanol (90:5:5 by volume

Sources & evidence

ORD record: ord-770e522bd0d947dfb1bbc17f7ecaf18f
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07538141B2

Reaction notes

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