Water → [2-Chloro-4-(trifluoromethyl)phenyl](cyclopropyl)methanol
Reaction equation
[CH:1]1([Mg]Br)[CH2:3][CH2:2]1.[Cl:6][C:7]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][C:8]=1[CH:9]=[O:10].O.C(OCC)(=O)C>C1COCC1.C(OCC)C>[Cl:6][C:7]1[CH:14]=[C:13]([C:15]([F:16])([F:17])[F:18])[CH:12]=[CH:11][C:8]=1[CH:9]([CH:1]1[CH2:3][CH2:2]1)[OH:10]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
84 ml (41.9 mmol) of 0.5N cyclopropylmagnesium bromide solution in THF were added to 5.83 g (30.0 mmol) of 2-chloro-4-(trifluoromethyl)benzaldehyde in 117 ml of diethyl ether at 0° C., and the mixture was warmed to RT and stirred at RT overnight. The reaction mixture was added to water and ethyl acetate, the phases were separated, the aqueous phase was extracted three times with ethyl acetate, and the combined organic phases were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated. The crude product was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate 95/5) to result in 5.00 g (61% of theory) of the title compound.
Workup
- customthe phases were separated
- extractionthe aqueous phase was extracted three times with ethyl acetate
- washthe combined organic phases were washed with saturated aqueous sodium chloride solution
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe crude product was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate 95/5)
Sources & evidence
- ORD record
- ord-714ca5c27df94993ba3b965d6df86a6b
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08063234B2
Reaction notes
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