Diethyl Ether → 2',4'-Difluoro-2-(2-methoxyethyl)thioacetophenone

HRID 613393

Reaction equation

HRID 613393 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.COCC[SH:17].C(=O)([O-])[O-].[K+].[K+].[CH3:24][CH2:25][O:26][CH2:27]C>CO>[F:12][C:6]1[CH:7]=[C:8]([F:11])[CH:9]=[CH:10][C:5]=1[C:3](=[S:17])[CH2:2][CH2:24][CH2:25][O:26][CH3:27]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 5880832-Chloro-1-(2,4-difluorophenyl)ethanoneHCID 30146442-Methoxyethanethiol

Product 1

HCID 187866342',4'-Difluoro-2-(2-methoxyethyl)thioacetophenoneYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-chloro-2',4'-difluoroacetophenone (2.7 g, 0.014 mol) and 2-methoxyethanethiol (J. Med. Chem., 39, 1253(1996)) (1.4 g, 0.015 mol) in methanol (50 ml), potassium carbonate (2.3 g, 0.016 mol) was added under ice cooling, followed by stirring at room temperature for 30 minutes. After the completion of the reaction, the insoluble matter was filtered off and the filtrate was distilled off under reduced pressure. The residue so obtained was diluted with ether, washed with water, dried over magnesium sulfate and distilled off under reduced pressure, whereby 2',4'-difluoro-2-(2-methoxyethyl)thioacetophenone (2.3 g, yield: 67.0%) was obtained as a colorless oil.

Workup

  1. customAfter the completion of the reaction
  2. filtrationthe insoluble matter was filtered off
  3. distillationthe filtrate was distilled off under reduced pressure
  4. customThe residue so obtained
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. distillationdistilled off under reduced pressure

Sources & evidence

ORD record
ord-35d90c19e4874bca853582f35f470620
Source dataset
uspto-grants-1999_12
Patent number
US06008239

Linked notes

Loading…