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 dry THF (50 mL) at 0° C., a solution of 2.4 M methyl magnesium bromide (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 NH4Cl solution. The organic was extracted with EtOAc (3×50 mL). The combined EtOAc layers were washed with brine and dried over Na2SO4. The resulting alcohol was obtained as an oil after flash chromatography using EtOAc:hexane=2:8 as the eluant.
Workup
- customThe reaction was quenched with saturated NH4Cl solution
- extractionThe organic was extracted with EtOAc (3×50 mL)
- washThe combined EtOAc layers were washed with brine
- dry with materialdried over Na2SO4
Sources & evidence
- ORD record
- ord-9a1bb05199f54be2b7b7cd02a6f352ce
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07910592B2
Reaction notes
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