1-(4-Chloro-3-fluorophenyl)propan-2-one → 1-(4-Chloro-3-fluorophenyl)-2-methylpropan-2-ol
Reaction equation
[CH3:1][Mg]Br.[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12](=[O:14])[CH3:13])=[CH:7][C:6]=1[F:15]>C1COCC1>[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([CH3:1])([OH:14])[CH3:13])=[CH:7][C:6]=1[F:15]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 76 °C
Procedure
To a solution of methylmagnesium bromide (100 mL, 100.0 mmol, 1.0 M in THF) was added a solution of 1-(4-chloro-3-fluorophenyl)propan-2-one (9.00 g, 48.20 mmol) in THF (20 mL) dropwise at 0° C. under N2 and the reaction mixture was heated at 76° C. for 12 h. It was then cooled to rt and quenched with saturated NH4Cl aqueous solution (50 mL) and the mixture was poured into water (200 mL). The resulting mixture was extracted with EtOAc (100 mL×4) and the combined organic phases were washed with brine (100 mL×2), dried over anhydrous Na2SO4 (50 g) and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=8:1) to give the title compound as yellow liquid (8.61 g, 88.2%).