Thiophenol → 5-Fluoro-3-(1-hydroxy-1-phenylpropyl)thiophenol

HRID 260435Notes

Reaction equation

HRID 260435 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.F[C:9]1[CH:14]=[C:13]([C:15]([C:25]2C=CC=C[CH:26]=2)([O:20][Si](C)(C)C)C(F)(F)F)[CH:12]=[C:11](F)[CH:10]=1.[F:32]C1C=C(C(C2SC=CN=2)=O)C=C(F)C=1.C1([Mg]Br)C=CC=CC=1.C([Mg]Br)=C>C1COCC1>[F:32][C:5]1[CH:4]=[C:3]([C:15]([OH:20])([C:13]2[CH:14]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:25][CH3:26])[CH:2]=[C:1]([SH:7])[CH:6]=1

Participants

7

Reactant 5

HCID 7969ThiophenolHCID 194269361,3-Difluoro-5-(1-phenyl-1-trimethylsilyloxy-2,2,2-trifluoroethyl)benzeneHCID 19426944(3,5-Difluorophenyl)(thiazol-2-yl)methanoneHCID 178418255HCID 178418255, compoundHCID 178418507HCID 178418507, compound

Product 1

HCID 194269825-Fluoro-3-(1-hydroxy-1-phenylpropyl)thiophenol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the procedure described for Thiophenol 2, Step 3 and Thiophenol 1, Steps 2 and 3 but substituting 3,5-difluoropropiophenone (Lancaster) for (3,5-difluorophenyl)(thiazol-2-yl)methanone and phenylmagnesium bromide in THF (Aldrich) for vinylmagnesium bromide as starting material the title compound was obtained.

Sources & evidence

ORD record
ord-11dab32254094a6caa5c35d76e3c749e
Source dataset
uspto-grants-1996_06
Patent number
US05527827

Reaction notes

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