Chloroacetone → 1-((3-Bromophenyl)thio)-2-propanone

HRID 1466761Notes

Reaction equation

HRID 1466761 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.Cl[CH2:10][C:11](=[O:13])[CH3:12].C(N(CC)C(C)C)(C)C>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([S:8][CH2:10][C:11](=[O:13])[CH3:12])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 80597m-BromobenzenethiolHCID 81531Diisopropylethylamine

Product 1

HCID 628049741-((3-Bromophenyl)thio)-2-propanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

3-Bromothiophenol (2.89 g, 15.29 mmol) and chloroacetone (1.278 mL, 16.06 mmol) were mixed in THF (80 mL) and cooled to 0° C. N,N-Diisopropylethylamine (6.65 mL, 38.23 mmol) was added and the reaction was stirred at 0° C. for five minutes then allowed to warm to room temperature and stirred overnight. The reaction was then extracted with EtOAc and H2O and the organic portion was concentrated to afford the title compound.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred overnight
  3. extractionThe reaction was then extracted with EtOAc and H2O
  4. concentrationthe organic portion was concentrated

Sources & evidence

ORD record
ord-1a0f80a2f66e4fca87f886ee97193c7d
Source dataset
uspto-grants-2015_04
Patent number
US09000025B2

Reaction notes

Loading…