Phenacyl bromide → 722516-74-7

HRID 2055919Notes

Reaction equation

HRID 2055919 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].C([O-])([O-])=O.[K+].[K+].[SH:17][C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=1)[C:21]([OH:23])=[O:22]>C(O)C>[O:4]=[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:2][S:17][C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=1)[C:21]([OH:23])=[O:22]

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 11430Potassium CarbonateHCID 95737Benzoic acid, 3-mercapto-

Product 1

HCID 59658539722516-74-7Yield 120.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To bromoacetophenone (250 mg, 1.16 mmole) and anhydrous K2CO3 (694 mg, 5.02 mmole) in ethanol, 193.6 mg (1.25 mmole) 3-mercaptobenzoic acid was added and the mixture refluxed overnight. The solvent was evaporated and water added to the solid residue. The basic aqueous solution was extracted with ethyl acetate to remove unreacted bromoacetophenone. The aqueous layer was acidified and extracted with ethyl acetate, dried, evaporated and the residue purified by flash chromatography using chloroform:methanol 95:5. Evaporation of the fractions resulted in a yellow powder (380 mg). M.S. m/s 271 (M−1)+. 1H NMR (DMSO) δ4.75 (2H, s, —CH2-), 7.39-7.7 (4H, m, 4×ArH), 7.75 (1H, d, ArH, J=5.61 Hz), 7.86 (1H, s, ArH), 8.02 (3H, d, ArH).

Workup

  1. temperaturethe mixture refluxed overnight
  2. customThe solvent was evaporated
  3. additionwater added to the solid residue
  4. extractionThe basic aqueous solution was extracted with ethyl acetate
  5. customto remove unreacted bromoacetophenone
  6. extractionextracted with ethyl acetate
  7. customdried
  8. customevaporated
  9. customthe residue purified by flash chromatography
  10. customEvaporation of the fractions

Sources & evidence

ORD record
ord-6bcb54695fac4e87ab0086bd176268d9
Source dataset
uspto-grants-2008_02
Patent number
US07332631B2

Reaction notes

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