Phenacyl bromide → ethanone, 2-[(4-chlorophenyl)thio]-1-phenyl-

HRID 1402918Notes

Reaction equation

HRID 1402918 reaction equation
[CH2:1](Br)[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3].[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([SH:18])=[CH:14][CH:13]=1>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.ClCCl.O>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([S:18][CH2:1][C:2]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[O:3])=[CH:14][CH:13]=1

Participants

6

Reactant 2

HCID 6259Phenacyl bromideHCID 7815p-Chlorothiophenol

Product 1

HCID 235035ethanone, 2-[(4-chlorophenyl)thio]-1-phenyl-Yield 56.1%

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of phenacyl bromide (1 g), 4-chlorothiophenol (1.37 g), and benzyl triethyl ammonium chloride (78 mg) in dichloromethane (20 ml) NaOH (0.61 g) in water (2 ml) was added. The mixture was stirred vigorously at rt for 16 h. After dilution with water (50 ml) the organic layer was separated, washed with brine (20 ml), dried (MgSO4), and evaporated. The crude was purified by column chromatography on silica gel (petrol ether/ethyl acetate 12:1) to provide 2-(4-chlorophenylthio)-1-phenylethanone (0.74 g) as pale yellow solid.

Workup

  1. customAfter dilution with water (50 ml) the organic layer was separated
  2. washwashed with brine (20 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe crude was purified by column chromatography on silica gel (petrol ether/ethyl acetate 12:1)

Sources & evidence

ORD record
ord-e58f0535ac894dd282b3b638b0dedfc8
Source dataset
uspto-grants-2014_12
Patent number
US08912186B2

Reaction notes

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