3',4',5'-Trifluoroacetophenone → 1-(3,5-Difluoro-4-(methylthio)phenyl)ethanone

HRID 47638Notes

Reaction equation

HRID 47638 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[C:8]([F:10])[C:7](F)=[C:6]([F:12])[CH:5]=1)=[O:3].[CH3:13][S-:14].[Na+]>C(#N)C>[F:12][C:6]1[CH:5]=[C:4]([C:2](=[O:3])[CH3:1])[CH:9]=[C:8]([F:10])[C:7]=1[S:14][CH3:13]

Participants

4

Reactant 2

HCID 27769073',4',5'-TrifluoroacetophenoneHCID 4378561Sodium methanethiolate

Product 1

HCID 227456341-(3,5-Difluoro-4-(methylthio)phenyl)ethanoneYield 73.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The 3,4,5-triflouroacetophenone (9.50 g, 54.6 mmol) and sodium thiomethoxide (4.60 g) were mixed together in acetonitrile (80 mL). The solution was stirred for 2 hour at ambient temperature. Solvent was removed in vacuo and the residue dissolved in ethyl acetate. The solution was extracted with water (2×100 mL), saturated ammonium chloride (2×100 mL) and dried over sodium sulfate. Solvent was removed in vacuo to yield 1-[3,5-difluoro-4-(methyl-thio)phenyl]ethanone as a yellow oil (8.08 g, 73%). 1H NMR (CDCl3/300 MHz) 7.46-7.43 (m, 2H), 2.58 (s, 3H), 2.56 (t, 3H, J=1). ESHRMS m/z 203.0357 (M+H+, Calcd 203.0342).

Workup

  1. customSolvent was removed in vacuo
  2. dissolutionthe residue dissolved in ethyl acetate
  3. extractionThe solution was extracted with water (2×100 mL), saturated ammonium chloride (2×100 mL)
  4. dry with materialdried over sodium sulfate
  5. customSolvent was removed in vacuo

Sources & evidence

ORD record
ord-92e54d2156664851b4a1f4eaa02196a9
Source dataset
uspto-grants-2004_03
Patent number
US06699884B2

Reaction notes

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