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

HRID 907077Notes

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, 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-077ac353bd0a471cbb5994080d6a1deb
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08013019B2

Reaction notes

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