3,4-Dibromothiophene → 3-Bromo-4-(propylsulfanyl)thiophene

HRID 2231609Notes

Reaction equation

HRID 2231609 reaction equation
[Br:1][C:2]1[C:6](Br)=[CH:5][S:4][CH:3]=1>C1(C)C(C)=CC=CC=1>[Br:1][C:2]1[C:6]([S:4][CH2:3][CH2:2][CH3:6])=[CH:5][S:4][CH:3]=1

Participants

3

Reactant 1

HCID 184523,4-Dibromothiophene

Product 1

HCID 142549413-Bromo-4-(propylsulfanyl)thiopheneYield 43.2%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 50 g of 3,4-dibromothiophene, 30 g of 85% potassium propyl mercaptide and 4.5 g of Carbowax®2000 in 50 ml of xylene was heated at reflux for 18 hours. The reaction was cooled, an additional 9 g of the mercaptide was added, and refluxing was continued for an additional 31 hours. After cooling, the mixture was filtered and the filtrate distilled to provide 10.6 g (21.3%) of 3-bromo-4-(propylthio)thiophene, bp 91°-102° C. (1.4 mm).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. temperatureThe reaction was cooled
  4. temperaturerefluxing
  5. temperatureAfter cooling
  6. filtrationthe mixture was filtered
  7. distillationthe filtrate distilled

Sources & evidence

ORD record
ord-ff8b76eb4c1a4de9a30674c2990da534
Source dataset
uspto-grants-1988_11
Patent number
US04783285

Reaction notes

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