Water → 5-Fluoro-3-(hexafluoro-2-hydroxyprop-2-yl)-1-(2-trimethylsilylethylthio)benzene

HRID 741804Notes

Reaction equation

HRID 741804 reaction equation
[CH3:1][Si:2]([CH3:7])([CH3:6])[CH2:3][CH2:4][SH:5].[H-].[Na+].[F:10][C:11]1[CH:16]=[C:15]([C:17]([OH:26])([C:22]([F:25])([F:24])[F:23])[C:18]([F:21])([F:20])[F:19])[CH:14]=[C:13](F)[CH:12]=1.O>CN(C=O)C>[F:10][C:11]1[CH:16]=[C:15]([C:17]([OH:26])([C:18]([F:19])([F:20])[F:21])[C:22]([F:24])([F:25])[F:23])[CH:14]=[C:13]([S:5][CH2:4][CH2:3][Si:2]([CH3:7])([CH3:6])[CH3:1])[CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2055212-(Trimethylsilyl)ethanethiolHCID 194269391,3-Difluoro-5-(hexafluoro-2-hydroxyprop-2-yl)benzene

Product 1

HCID 194269565-Fluoro-3-(hexafluoro-2-hydroxyprop-2-yl)-1-(2-trimethylsilylethylthio)benzeneYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
70 °C

Procedure

2-Trimethylsilylethane thiol (2.9 g, 21.9 mmol) was added dropwise to a suspension of NaH (1.8 g, 43.8 mmol) in dry DMF (60 mL) and stirred for 20 min. Then 1,3-difluoro-5-(hexafluoro-2-hydroxyprop2-yl)benzene (Step 1) was added in dry DMF and the resulting reaction mixture was heated at 70° C. for 16 h. The reaction mixture was then added carefully to H2O and extracted with EtOAc. The combined organic phases were washed with brine, dried and evaporated to give a residue which was chromatographed on silica gel, eluting with 95:5 mixture of hexane:EtOAc to afford the title compound (3.2 g, 55%).

Workup

  1. customthe resulting reaction mixture
  2. extractionextracted with EtOAc
  3. washThe combined organic phases were washed with brine
  4. customdried
  5. customevaporated
  6. customto give a residue which
  7. customwas chromatographed on silica gel
  8. washeluting with 95:5 mixture of hexane

Sources & evidence

ORD record
ord-5e299280aa2d486986401e4eccfb51d5
Source dataset
uspto-grants-1996_09
Patent number
US05552437

Reaction notes

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