Thiophenol → [(5-Bromopentyl)thio]benzene

HRID 462251Notes

Reaction equation

HRID 462251 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]Br.[OH-].[Na+]>C(O)C>[Br:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][S:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 81001,5-DibromopentaneHCID 14798Sodium Hydroxide

Product 1

HCID 12272162[(5-Bromopentyl)thio]benzene

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 20 ml (0.2 mol) of thiophenol and 50.6 g (0.22 mol) of 1,5-dibromopentane in 200 ml of ethanol is heated to 40° C whilst stirring and 40 ml (0.2 mol) of 5N NaOH are added dropwise. Thereafter the mixture is stirred for 2 hours and after standing overnight the alcohol is evaporated in vacuo, the residue is extracted with methylene chloride and the extract is washed 3 to 4 times with water, dried and evaporated. A yellow oil is obtained in quantitative yield.

Workup

  1. stirringThereafter the mixture is stirred for 2 hours
  2. customthe alcohol is evaporated in vacuo
  3. extractionthe residue is extracted with methylene chloride
  4. washthe extract is washed 3 to 4 times with water
  5. customdried
  6. customevaporated
  7. customA yellow oil is obtained in quantitative yield

Sources & evidence

ORD record
ord-af4e645659cd4afe81df3efd4531801a
Source dataset
uspto-grants-1977_12
Patent number
US04065584

Reaction notes

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