Dimethylformamide → Methyl 2-acetylthio-3-(4-methylphenyl)propionate

HRID 466968Notes

Reaction equation

HRID 466968 reaction equation
Br[CH:2]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)[C:3]([O:5][CH3:6])=[O:4].[C:15]([O-:18])(=[S:17])[CH3:16].[K+].CN(C=O)C>O>[C:15]([S:17][CH:2]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)[C:3]([O:5][CH3:6])=[O:4])(=[O:18])[CH3:16]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 19812946Methyl 2-bromo-3-(4-methylphenyl)propanoateHCID 23670855Potassium ethanethioate

Product 1

HCID 19812945Methyl 2-acetylthio-3-(4-methylphenyl)propionateYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 2-bromo-3-(4-methylphenyl)propionate (25.7 g), potassium thioacetate (CH3COSK) (13.7 g) and DMF (120 ml) was stirred for an hour at room temperature. The mixture was poured into water and extracted with ether. The ethereal layer was washed with water, dried (MgSO4) and concentrated to give methyl 2-acetylthio-3-(4-methylphenyl)propionate (25.2 g, 100%) as an oil.

Workup

  1. extractionextracted with ether
  2. washThe ethereal layer was washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-91ae9cbf435b437daba3612667980f26
Source dataset
uspto-grants-1992_10
Patent number
US05158943

Reaction notes

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