Water → [(5-Chloropentyl)sulfanyl]benzene

HRID 344267Notes

Reaction equation

HRID 344267 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][Cl:14].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:1]1([S:7][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][Cl:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 960701-Bromo-5-chloropentane

Product 1

HCID 13427894[(5-Chloropentyl)sulfanyl]benzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Benzenethiol (3.0 g), 1-bromo-5-chloropentane (5.7 g) and potassium carbonate (4.15 g) were suspended in N,N-dimethylformamide (50 ml), and the mixture was stirred at 50° C. for 5 hr. After cooling, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried and the solvent was evaporated under reduced pressure. Thus, 5-phenylthiopentyl chloride was obtained. This compound was dissolved in formic acid (50 ml) and 2 equivalents of 30% aqueous hydrogen peroxide solution was added thereto, and the mixture was stirred at room temperature for 6 hr.

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. customdried
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-4d0a5718b07d4b8291a89539723afbdb
Source dataset
uspto-grants-1999_01
Patent number
US05864039

Reaction notes

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