2'-Fluoro-4'-methoxyacetophenone → 2-(2-Fluoro-4-methoxyphenyl)-2-propanol
Reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10](=[O:12])[CH3:11].[CH3:13][Mg+].[Br-]>C1COCC1>[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]([OH:12])([CH3:13])[CH3:11]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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 mmol, 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 was extracted with ethyl acetate (3×50 ml). The combined ethyl acetate layers were washed with brine and dried over sodium sulfate. The resulting alcohol 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 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-77634d92baf34aa68cefe50f245a634f
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08735435B2
Reaction notes
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