Tetrahydrofuran → 3-Fluoro-5-phenylthiophenol

HRID 1901113Notes

Reaction equation

HRID 1901113 reaction equation
C[Si](C)(C)CC[S:5][C:6]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:9]=[C:8]([F:18])[CH:7]=1.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-].C1COCC1.CCOC(C)=O>CN(C=O)C>[F:18][C:8]1[CH:7]=[C:6]([SH:5])[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:9]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 57070644S-(2-Trimethylsilylethyl)-3-fluoro-5-phenylthiophenol

Product 1

HCID 233702173-Fluoro-5-phenylthiophenol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To S-(2-trimethylsilylethyl)-3-fluoro-5-phenylthiophenol (2.4 g) in DMF (50 mL) was added Bu4NF (16 mL of a 1M THF solution). After 90 min., EtOAc was added and this solution was washed with 1N HCl, H2O and brine. Concentration and chromatography (silica gel; hexane/EtOAc (9:1)) provided the title compound as a liquid.

Workup

  1. washthis solution was washed with 1N HCl, H2O and brine
  2. concentrationConcentration and chromatography (silica gel; hexane/EtOAc (9:1))

Sources & evidence

ORD record
ord-fde2686be1c44a5f80c8583791c536f1
Source dataset
uspto-grants-1996_11
Patent number
US05576338

Reaction notes

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