Phenacyl bromide → HCID 59658556, compound

HRID 2055922Notes

Reaction equation

HRID 2055922 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:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=1>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:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 11430Potassium CarbonateHCID 957384-Mercaptobenzoic acid

Product 1

HCID 59658556HCID 59658556, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To bromoacetophenone (322.8 mg, 1.62 mmole) and anhydrous K2CO3 (896 mg, 6.48 mmole) in ethanol (20 ml), 250 mg (1.62 mmole) 4-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 to yield a precipitate which was filtered and dried (356 mg). m/z 271 (M−1)+1H NMR (DMSO) δ 4.75 (2H, s, —CH2-), 7.35-7.72 (5H, m, 5×ArH), 7.82 (2H, d, 2×ArH), 8.05 (2H, d, 2×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. customto yield a precipitate which
  7. filtrationwas filtered
  8. customdried (356 mg)

Sources & evidence

ORD record
ord-b8a8378d7e174e76beb98c05ed76d56c
Source dataset
uspto-grants-2008_02
Patent number
US07332631B2

Reaction notes

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