2-Chloro-1-(2,4-difluorophenyl)ethanone → 1-(2,4-Difluorophenyl)-2-(methylsulfanyl)ethan-1-one

HRID 611813Notes

Reaction equation

HRID 611813 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=1[F:12])=[O:4].[CH3:13][SH:14].[Na]>CO>[F:12][C:6]1[CH:7]=[C:8]([F:11])[CH:9]=[CH:10][C:5]=1[C:3](=[O:4])[CH2:2][S:14][CH3:13]

Participants

4

Reactant 2

HCID 5880832-Chloro-1-(2,4-difluorophenyl)ethanone2×HCID 45051789Methylmercaptan sodium

Product 1

HCID 106557171-(2,4-Difluorophenyl)-2-(methylsulfanyl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 500 ml solution of 50 g (0.262 mol) of 2-chloro-2',4'-difluoroacetophenone [Compound (4)-1] in methanol, 147 g (0.314 mol) of a 15% aqueous solution of sodium methylmercaptan were added dropwise under ice cooling, followed by stirring at room temperature for 2 hours. The solvent was distilled off under reduced pressure. Water was then added to the reaction mixture and they were mixed. The resulting mixture was extracted with chloroform. The extract was washed successively with water and saturated saline and then, dried over anhydrous magnesium sulfate. The solvent was thereafter distilled off under reduced pressure. The oil so obtained was distilled under reduced pressure (93-95° C., 3 mmHg), whereby 47.3 g of the title Compound (2a-1) were obtained as a colorless oil (yield: 89.2%).

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. additionWater was then added to the reaction mixture and they
  3. additionwere mixed
  4. extractionThe resulting mixture was extracted with chloroform
  5. washThe extract was washed successively with water and saturated saline
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was thereafter distilled off under reduced pressure
  8. customThe oil so obtained
  9. distillationwas distilled under reduced pressure (93-95° C., 3 mmHg)

Sources & evidence

ORD record
ord-22a76757d5c4469b9bf8708375469fdb
Source dataset
uspto-grants-1999_12
Patent number
US06002028

Reaction notes

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