Water → HCID 70201361, compound

HRID 466969Notes

Reaction equation

HRID 466969 reaction equation
[SH:1][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].Br[CH:16]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)C(O)=O.[C:26](=O)([O-:28])[O-:27].[K+].[K+].O>CN(C=O)C>[C:26]([C:2]([S:1][CH2:16][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([CH2:7][C:8]1[CH:9]=[CH:10][C:11]([CH3:14])=[CH:12][CH:13]=1)[C:3]([O:5][CH3:6])=[O:4])([OH:28])=[O:27]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 97919Bromo(phenyl)acetic acidHCID 19812935HCID 19812935, compound

Product 1

HCID 70201361HCID 70201361, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of methyl 2-mercapto-3-(4-methylphenyl)propionate (17.5 g) in DMF (30 ml) was added dropwise to a mixture of α-bromophenylacetic acid (17.0 g), potassium carbonate (34.4 g) and DMF (120 ml), followed by stirring for an hour at room temperature. The reaction mixture was poured into water (300 ml) and extracted with ether. The aqueous layer was acidified with conc. HCl and extracted with ether. The ethereal layer was washed with water, dried (MgSO4) and concentrated to give methyl 2-(carboxy)(phenyl)methylthio-3-(4-methylphenyl)propionate (25.7 g, 90%) as an oil.

Workup

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

Sources & evidence

ORD record
ord-cfb1b4c5e7a24a65b95c703f35af3361
Source dataset
uspto-grants-1992_10
Patent number
US05158943

Reaction notes

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