Water → HCID 57702362, compound
Reaction equation
[Mg].[F:2][C:3](S(C1C=CC=CC=1)(=O)=O)(S(C1C=CC=CC=1)(=O)=O)[CH:4]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([CH3:16])[CH3:15])=[CH:9][CH:8]=1)[CH2:5][OH:6].O>C(Br)Br.C[Si](Cl)(C)C.CO>[F:2][CH2:3][CH:4]([C:7]1[CH:8]=[CH:9][C:10]([CH2:13][CH:14]([CH3:16])[CH3:15])=[CH:11][CH:12]=1)[CH2:5][OH:6]Participants
Conditions
- Temperature
- 0 °C
Procedure
One drop of CH2Br2 and then 1 drop of TMSCl were charged into a 5 mL solution of magnesium ribbon (707 mg, 29.1 mmol, 45.0 eq) in MeOH. The solution was cooled to 0° C., and then a 5 mL solution of 3-fluoro-2-(4-isobutylphenyl)-3,3-bis(phenylsulfonyl)propan-1-ol (317 mg, 0.646 mmol, 1.0 eq) in MeOH was added dropwise thereto. The solution was stirred for 2 hours at 0° C., and then water was charged thereto to stop the reaction. The aqueous solution was acidified using 1 M HCR. The aqueous layer was extracted with methylene chloride and then the extract was dried with anhydrous sodium sulfate. The solvent was removed under reduced pressure by distillation, and then the resultant product was purified by column chromatography (hexane:ethyl acetate=7:3) to obtain 3-fluoro-2-(4-isobutylphenyl)propan-1-ol (119 mg, 87%).
Workup
- customthe reaction
- extractionThe aqueous layer was extracted with methylene chloride
- dry with materialthe extract was dried with anhydrous sodium sulfate
- customThe solvent was removed under reduced pressure by distillation
- customthe resultant product was purified by column chromatography (hexane:ethyl acetate=7:3)
Sources & evidence
- ORD record
- ord-dbbc51a296ea4c54930afb867be67959
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07638654B2
Reaction notes
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