p-Chlorophenacyl bromide → 1-(4-Chlorophenyl)-2-(methylsulfanyl)ethan-1-one

HRID 1875851Notes

Reaction equation

HRID 1875851 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1)=[O:4].[CH3:12][S-:13].[Na+]>O1CCCC1.C(OCC)C>[Cl:11][C:8]1[CH:9]=[CH:10][C:5]([C:3](=[O:4])[CH2:2][S:13][CH3:12])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 68303p-Chlorophenacyl bromideHCID 4378561Sodium methanethiolate

Product 1

HCID 143730331-(4-Chlorophenyl)-2-(methylsulfanyl)ethan-1-oneYield 86.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 2-bromo-1-(4-chlorophenyl)ethanone (1, 20 g, 86 mmol) in tetrahydrofuran (250 ml) was added sodium methanethiolate (7.2 g, 103 mmol) in tetrahydrofuran (250 ml) at −40° C. and the mixture was stirred for 1 hour. The mixture was diluted with diethyl ether and filtered off, and the filtrate was washed with brine. The solvent was evaporated off under the reduced pressure, and the residue was subjected to silica gel column chromatography (Biotage) to obtain 15 g of the title compound.

Workup

  1. filtrationfiltered off
  2. washthe filtrate was washed with brine
  3. customThe solvent was evaporated off under the reduced pressure

Sources & evidence

ORD record
ord-f3555e32fd3340799a252ea569e7e707
Source dataset
uspto-grants-2012_11
Patent number
US08309584B2

Reaction notes

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