Hydrochloric Acid → 1,3-Difluoro-5-[3-hydroxy-3-(thiazol-2-yl)propen-3-yl]benzene

HRID 741807Notes

Reaction equation

HRID 741807 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]([C:11]2[S:12][CH:13]=[CH:14][N:15]=2)=[O:10])[CH:5]=[C:6]([F:8])[CH:7]=1.[CH:16]([Mg]Br)=[CH2:17].Cl>C1COCC1>[F:8][C:6]1[CH:5]=[C:4]([C:9]([OH:10])([C:11]2[S:12][CH:13]=[CH:14][N:15]=2)[CH:16]=[CH2:17])[CH:3]=[C:2]([F:1])[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 19426944(3,5-Difluorophenyl)(thiazol-2-yl)methanoneHCID 178418507HCID 178418507, compound

Product 1

HCID 194269861,3-Difluoro-5-[3-hydroxy-3-(thiazol-2-yl)propen-3-yl]benzeneYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (3,5-difluorophenyl)(thiazol-2-yl)methanone (1 g, 4.4 mmol, Step 2) in dry THF (40 mL) was added at 0° C. (4.4 mL, 4.4 mmol) of a 1.0M THF solution of vinyl magnesium bromide (Aldrich). The reaction mixture was stirred for 30 min. and then transferred to a 1N aqueous HCl solution. The resulting mixture was extracted with EtOAc and the combined organic phase were washed with brine, dried over MgSO4 and evaporated to give a residue which was chromatographed on silica gel eluting with 85:15 mixture of hexane: EtOAc to afford 635 mg (56%) of the title compound.

Workup

  1. extractionThe resulting mixture was extracted with EtOAc
  2. washthe combined organic phase were washed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customto give a residue which
  6. customwas chromatographed on silica gel eluting with 85:15 mixture of hexane

Sources & evidence

ORD record
ord-79f867496534423ca0ced42de63f5fc5
Source dataset
uspto-grants-1996_09
Patent number
US05552437

Reaction notes

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