Water → 5-Fluoro-3-(hexafluoro-2-hydroxyprop-2-yl)thiophenol
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:15]([OH:24])([C:20]([F:23])([F:22])[F:21])[C:16]([F:19])([F:18])[F:17])[CH:5]=[C:6]([S:8]CC[Si](C)(C)C)[CH:7]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([C:15]([OH:24])([C:16]([F:17])([F:18])[F:19])[C:20]([F:21])([F:22])[F:23])[CH:5]=[C:6]([SH:8])[CH:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a solution of 5-fluoro-3-(hexafluoro-2-hydroxyprop-2-yl)-1-(2-trimethylsilylethylthio)benzene (1 g, 2.54 mmol Step 2) in dry DMF (20 mL) was added tetrabutylammonium fluoride (1M in THF) (Aldrich) (6.4 mL, 6.4 mmol) and the reaction mixture was heated at 60° C. for 30 min. The reaction mixture was then added to H2O and extracted with EtOAc. The combined organic phase were washed with brine, dried and evaporated to give a residue which was chromatographed on silica gel eluting with 8:2 mixture of hexane:EtOAc to afford the title compound (330 mg, 44%).
Workup
- extractionextracted with EtOAc
- washThe combined organic phase were washed with brine
- customdried
- customevaporated
- customto give a residue which
- customwas chromatographed on silica gel eluting with 8:2 mixture of hexane
Sources & evidence
- ORD record
- ord-8f27d294cad544aa9f3b8a57c67fd182
- Source dataset
- uspto-grants-1996_06
- Patent number
- US05527827
Reaction notes
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