2'-Fluoro-4'-methoxyacetophenone → 2-(2-Fluoro-4-methoxyphenyl)-2-propanol

HRID 537956Notes

Reaction equation

[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1[F:12])=[O:3].[CH3:13][Mg+].[Br-]>C1COCC1>[F:12][C:5]1[CH:6]=[C:7]([O:10][CH3:11])[CH:8]=[CH:9][C:4]=1[C:2]([OH:3])([CH3:13])[CH3:1]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2-fluoro-4-methoxyacetophenone (4.45 g, 26.5 mmol) in THF (50 mL) at 0° C., a solution of 2.4 M MeMgBr (11.6 mL, 27.8 mmol) was added. The mixture was stirred at 0° C. and then room temperature for 4 h. The reaction was quenched with saturated ammonium chloride solution. The organic layer was extracted with ethyl acetate (3×50 mL). The combined ethyl acetate layers were washed with brine and dried over sodium sulfate. The title compound was obtained as an oil after flash column using EtOAc:hexane=2:8 as the elute.

Workup

customThe reaction was quenched with saturated ammonium chloride solution
extractionThe organic layer was extracted with ethyl acetate (3×50 mL)
washThe combined ethyl acetate layers were washed with brine
dry with materialdried over sodium sulfate

Sources & evidence

ORD record: ord-0d16f08802c74141b054e39124a70507
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865707B2

Reaction notes

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