Water → 1069051-44-0
Reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.S([O-])([O-])(=O)=O.[Na+].[Na+].[F:17][C:18]([F:26])(S(F)(=O)=O)C(O)=O.O>C(#N)C>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][O:7][CH:18]([F:26])[F:17])=[CH:4][CH:3]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 45 °C
Procedure
To a solution of 4-bromobenzyl alcohol (5.6 g) in acetonitrile (15 ml), sodium sulfate (0.28 g) was added. While warmed to 45° C., 2,2-difluoro-2-(fluorosulfonyl)acetic acid (1.78 g) was slowly dropwise added, and the mixture was heated and refluxed at 45° C. for 4 hours. The reaction solution was poured into water, the mixture was extracted with diethyl ether and the organic layer was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off in vacuo and the residue obtained was purified with silica gel column chromatography (hexane:ethyl acetate=19:1 to 17:3) to afford the above-identified compound (0.88 g).
Workup
- temperaturethe mixture was heated
- temperaturerefluxed at 45° C. for 4 hours
- extractionthe mixture was extracted with diethyl ether
- washthe organic layer was washed with water
- dry with materialdried over anhydrous sodium sulfate
- distillationThe solvent was distilled off in vacuo
- customthe residue obtained
- customwas purified with silica gel column chromatography (hexane:ethyl acetate=19:1 to 17:3)
Sources & evidence
- ORD record
- ord-5c13996026544dea9693030aad55b6da
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08293781B2
Reaction notes
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