2,3-Dichloropropene → (4-Bromophenyl)(2-chloroallyl)sulfane

HRID 330281Notes

Reaction equation

HRID 330281 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[Cl:15][C:16]([CH2:18]Cl)=[CH2:17]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:18][C:16]([Cl:15])=[CH2:17])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 65652,3-DichloropropeneHCID 11430Potassium CarbonateHCID 660494-Bromothiophenol

Product 1

HCID 14819351(4-Bromophenyl)(2-chloroallyl)sulfaneYield 67%

Procedure

According to the procedure of W. K. Anderson et al., J. Chem. Soc., Perkin 1, 1 (1976) a mixture of 4-bromothiophenol (40.0 g, 0.211 mol) and K2CO3 (35.3 g, 0.254 mol) was heated at reflux for 1 hour. 2,3-Dichloro-1-propene (23.5 g, 0.211 mol) was added. The resulting mixture was heated at reflux for 2 hours, cooled and concentrated. The mixture was diluted with H2O and extracted with ether (3×150 mL). The combined extracts were dried (MgSO4), and concentrated to give an oil. Distillation under high vacuum gave 37.2 g (67%) of product as a colorless liquid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hour
  3. temperatureThe resulting mixture was heated
  4. temperatureat reflux for 2 hours
  5. temperaturecooled
  6. concentrationconcentrated
  7. additionThe mixture was diluted with H2O
  8. extractionextracted with ether (3×150 mL)
  9. dry with materialThe combined extracts were dried (MgSO4)
  10. concentrationconcentrated
  11. customto give an oil
  12. distillationDistillation under high vacuum

Sources & evidence

ORD record
ord-aabe4721e9b941f08963a1cf7f68b8b1
Source dataset
uspto-grants-1990_01
Patent number
US04895860

Reaction notes

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