Thiophenol → 5-Fluoro-3-[1-hydroxy-1-(thiazol-2-yl)propyl]thiophenol

HRID 260434Notes

Reaction equation

HRID 260434 reaction equation
C1([SH:7])C=CC=CC=1.F[C:9]1[CH:10]=[C:11]([C:16]([C:18]2[S:19][CH:20]=[CH:21][N:22]=2)=[O:17])[CH:12]=[C:13]([F:15])[CH:14]=1.[CH2:23]([Mg]Br)[CH3:24].C([Mg]Br)=C>C1COCC1>[F:15][C:13]1[CH:12]=[C:11]([C:16]([OH:17])([C:18]2[S:19][CH:20]=[CH:21][N:22]=2)[CH2:23][CH3:24])[CH:10]=[C:9]([SH:7])[CH:14]=1

Participants

6

Reactant 4

HCID 7969Thiophenol3×HCID 19426944(3,5-Difluorophenyl)(thiazol-2-yl)methanoneHCID 178418443HCID 178418443, compoundHCID 178418507HCID 178418507, compound

Product 1

HCID 194269595-Fluoro-3-[1-hydroxy-1-(thiazol-2-yl)propyl]thiophenol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the procedure described for Thiophenol 2, Step 3 and thiophenol 5, Steps 2 and 3 but substituting the ketone from Thiophenol 5, Step 1 for (3,5-difluorophenyl)(thiazol-2-yl)methanone and ethylmagnesium bromide in THF (Aldrich) for vinylmagnesium bromide as starting material the title compound was obtained. Mass spec. 270 (MH+).

Sources & evidence

ORD record
ord-7c59a03e32054839bb55be7f48d8e39e
Source dataset
uspto-grants-1996_06
Patent number
US05527827

Reaction notes

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