Thiophenol → [(3-Chloro-2-methylpropyl)sulfanyl]benzene

HRID 462250Notes

Reaction equation

HRID 462250 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:9][CH:10]([CH3:13])[CH2:11][Cl:12].[OH-].[Na+]>C(O)C>[C:1]1([S:7][CH2:9][CH:10]([CH3:13])[CH2:11][Cl:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 14798Sodium HydroxideHCID 955661-Bromo-3-chloro-2-methylpropane

Product 1

HCID 12573586[(3-Chloro-2-methylpropyl)sulfanyl]benzeneYield 97.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 22 g (0.2 mol) of thiophenol and 37.7 g (0.22 mol) of 3-bromo-1-chloro-2-methylpropane in 200 ml of ethanol is stirred at 40° C and 40 ml (0.2 mol) of 5N sodium hydroxide solution is added dropwise. The mixture is stirred for a further 2 hours at 40° C and evaporated to dryness in vacuo, the residue is extracted with methylene chloride and the extract is washed with water, dried and evaporated in vacuo. 39 g (97%) of a yellow oil are obtained.

Workup

  1. stirringThe mixture is stirred for a further 2 hours at 40° C
  2. customevaporated to dryness in vacuo
  3. extractionthe residue is extracted with methylene chloride
  4. washthe extract is washed with water
  5. customdried
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-c3e0945c54d74585a2e00cf4e7e1d543
Source dataset
uspto-grants-1977_12
Patent number
US04065584

Reaction notes

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