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

HRID 1450502Notes

Reaction equation

HRID 1450502 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 45min 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-393e749c4d714c248d2930b667945919
Source dataset
uspto-grants-1997_02
Patent number
US05602163

Reaction notes

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