Chloroacetone → 1-((4-Bromophenyl)thio)propan-2-one

HRID 487984Notes

Reaction equation

HRID 487984 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[OH-].[Na+].Cl[CH2:12][C:13](=[O:15])[CH3:14]>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:12][C:13](=[O:15])[CH3:14])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 14798Sodium HydroxideHCID 660494-Bromothiophenol

Product 1

HCID 8219021-((4-Bromophenyl)thio)propan-2-oneYield 104.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 4-bromothiophenol (5.09 g, 26.9 mmol) in NaOH (1.08 g, 26.9 mmol) and water (32 ml) was added chloroacetone (2.17 ml, 27.3 mmol) and the mixture was stirred under nitrogen for 45 min before extracting with ether, washing with water, drying (Na2SO4) and evaporating in vacuo, leaving 6.89 g (100%) of the title compound as a white solid, δ (CDCl3) 2.27 (3H, s), 3.65 (2H, s), 7.20 (2H, d, J=8.5 Hz), 7.41 (2H, d, J=8.5 Hz).

Workup

  1. extractionbefore extracting with ether
  2. washwashing with water
  3. dry with materialdrying (Na2SO4)
  4. customevaporating in vacuo

Sources & evidence

ORD record
ord-c1982fcc1abe4d62a6efe6616df2da46
Source dataset
uspto-grants-1994_03
Patent number
US05298520

Reaction notes

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