Water → ((2-Chloroethyl)thio)benzene

HRID 446192

Reaction equation

HRID 446192 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O-]CC.[Na+].Br[CH2:13][CH2:14][Cl:15].O>C(O)C>[C:1]1([S:7][CH2:13][CH2:14][Cl:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 78491-Bromo-2-ChloroethaneHCID 7969ThiophenolHCID 2723922Sodium ethoxide

Product 1

HCID 21702((2-Chloroethyl)thio)benzeneYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Benzenethiol (15.0 g, 0.136 mol) was added to the solution of sodium ethoxide (0.20 mol) in 200 ml of anhydrous ethanol, and the mixture was stirred at room temperature for 15 minutes and then added to the solution of 1-bromo-2-chloroethane in 100 ml of ethanol. The resultant mixture was stirred at room temperature for 3 hours and poured into 300 ml of water. The mixture was extracted three times with ether and the combined organic layer was dried over magnesium sulfate. After removal of the solvent, the compound was purified by flash chromatography using heptane/ethyl acetate (100 to 97/3) as eluent in a yield of 74%.

Workup

  1. extractionThe mixture was extracted three times with ether
  2. dry with materialthe combined organic layer was dried over magnesium sulfate
  3. customAfter removal of the solvent
  4. customthe compound was purified by flash chromatography

Sources & evidence

ORD record
ord-9c8d7da7a00d4632ad6a1a5d015ca6a6
Source dataset
uspto-grants-2013_07
Patent number
US08476450B2

Linked notes

Loading…