1-(3,4-Difluorophenyl)ethan-1-one → 2-(3,4-Difluorophenyl)propan-2-ol
Reaction equation
[CH2:1]([Mg]Br)C.[F:5][C:6]1[CH:7]=[C:8]([C:13](=[O:15])[CH3:14])[CH:9]=[CH:10][C:11]=1[F:12].CCCCCC.CCOC(C)=O>C(OCC)C>[F:5][C:6]1[CH:7]=[C:8]([C:13]([OH:15])([CH3:1])[CH3:14])[CH:9]=[CH:10][C:11]=1[F:12]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of ethylmagnesium bromide in ether (38.0 mL, 38.0 mmol) at 0° C., was added a solution of 3′,4′-difluoroacetophenone (5.0 g, 32.0 mmol) in diethyl ether (35 mL). The reaction mixture was stirred at 0° C. for 1 h when TLC analysis indicated that the reaction was complete (Rf=0.3, 3:1 hexane/EtOAc). The reaction was quenched carefully by adding 38 mL of water. It was extracted with diethyl ether (2×30 mL), washed with Rochelle's salt followed by brine and the organic layer was dried over Na2SO4. The solvent was removed in vacuo after filtration and 2-(3,4-difluorophenyl)propan-2-ol was obtained as a colorless oil (crude wt.=5.4 g, 97%) which looked >90% pure by NMR. It was used in the next step without purification.
Workup
- customThe reaction was quenched carefully
- additionby adding 38 mL of water
- extractionIt was extracted with diethyl ether (2×30 mL)
- washwashed with Rochelle's salt
- dry with materialthe organic layer was dried over Na2SO4
- customThe solvent was removed in vacuo
- filtrationafter filtration
Sources & evidence
- ORD record
- ord-993a83a2b2cf465cb271f19412e1acdc
- Source dataset
- uspto-grants-2003_09
- Patent number
- US06620815B1
Reaction notes
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