Bromine → 2-Bromo-1-phenyl-2-(phenylthio)ethanone

HRID 2359952Notes

Reaction equation

HRID 2359952 reaction equation
[C:1]1([C:7](=[O:16])[CH2:8][S:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:17]Br>C(O)(=O)C>[Br:17][CH:8]([S:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[O:16]

Participants

4

Reactant 2

HCID 24408BromineHCID 85338Phenacyl phenyl sulfide

Product 1

HCID 156512352-Bromo-1-phenyl-2-(phenylthio)ethanoneYield 100%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 1-phenyl-2-(phenylthio)ethanone (2.1 g) in acetic acid (20 mL) was added bromine (0.5 mL), and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure, water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound as a yellow oil (yield 2.9 g, about 100%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, water
  2. additionwas added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e09a6ea6790347ebb7e27b97f2e2a13f
Source dataset
uspto-grants-2014_04
Patent number
US08686010B2

Reaction notes

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