1-(4-Bromophenyl)-2,2-difluoroethan-1-one → 2-(4-Bromophenyl)-1,1-difluoropropan-2-ol
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:12])[CH:9]([F:11])[F:10])=[CH:4][CH:3]=1.[CH3:13][Mg]Cl>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:12])([CH3:13])[CH:9]([F:11])[F:10])=[CH:6][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 1-(4-bromophenyl)-2,2-difluoroethanone (2.5 g, 10.6 mmol) in THF (60 mL) was added methylmagnesium chloride (10 mL, 30 mmol; 3 M in THF) at 0° C. over ˜10 min and the mixture was stirred at 0° C. for 1 h. A mini-worked up showed starting material remained and more methylmagnesium chloride (5 mL, 15 mmol, 3 M in THF) was added. After further stirred for 15 min., the mixture was quenched with H2O, carefully acidified with 1 M HCl (100 mL) and extracted with Ethyl acetate. Purification by combi-flash chromatography (120 g column; eluted with hexanes—Ethyl acetate (5% -25%) in 20 min.; flow rate: 70 mL/min and collected 25 mL/fraction) yielded the title compound as a colorless liquid.
Workup
- stirringAfter further stirred for 15 min.
- customthe mixture was quenched with H2O
- extractionextracted with Ethyl acetate
- customPurification
- washby combi-flash chromatography (120 g column; eluted with hexanes—Ethyl acetate (5% -25%) in 20 min.; flow rate: 70 mL/min and collected 25 mL/fraction)
Sources & evidence
- ORD record
- ord-c992a20fca0a4486bf1cab5b4cfb00e9
- Source dataset
- uspto-grants-2008_08
- Patent number
- US07407959B2
Reaction notes
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