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

HRID 523551Notes

Reaction equation

HRID 523551 reaction equation
Cl[CH2:2][C:3](=[O:5])[CH3:4].C(=O)([O-])[O-].[K+].[K+].[Br:12][C:13]1[CH:18]=[CH:17][C:16]([SH:19])=[CH:15][CH:14]=1.CCCCCC>CN(C=O)C>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([S:19][CH2:2][C:3](=[O:5])[CH3:4])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 6571ChloroacetoneHCID 8058HexaneHCID 11430Potassium CarbonateHCID 660494-Bromothiophenol

Product 1

HCID 8219021-((4-Bromophenyl)thio)propan-2-oneYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Chloro-propan-2-one (1.0 g, 11.63 mmol) and potassium carbonate (2.9 g, 21.15 mmol) were added to a solution of 4-bromo-benzenethiol (2.0 g, 10.58 mmol) in DMF (5.0 mL) at 0° C. The resulting mixture was stirred at room temperature overnight. The reaction was monitored by TLC (100% hexane). The reaction mixture quenched with ice and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated to yield the crude product. Purification by column chromatography on silica gel (2% methanol in chloroform) afforded 2.0 g of the product (80% yield).

Workup

  1. customThe reaction mixture quenched with ice
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. customto yield the crude product
  6. customPurification by column chromatography on silica gel (2% methanol in chloroform)

Sources & evidence

ORD record
ord-ef30fcd53f7146e5b9b1234b57f83962
Source dataset
uspto-grants-2016_05
Patent number
US09339501B2

Reaction notes

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