2-Chlorothiophene → trans 3-Bromocinnamoyl chloride

HRID 1105608Notes

Reaction equation

HRID 1105608 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)/[CH:5]=[CH:6]/[C:7](O)=[O:8].S1C=CC=C1[Cl:18]>C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)/[CH:5]=[CH:6]/[C:7]([Cl:18])=[O:8]

Participants

4

Reactant 2

HCID 72992-ChlorothiopheneHCID 776461m-Bromocinnamic acid

Product 1

HCID 14959106trans 3-Bromocinnamoyl chlorideYield 99%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of trans 3-bromocinnamic acid (m.p. 177°-179° C; 11.4 g), thienyl chloride (11.9 g) and dry benzene (150 ml) was heated at reflux for 2 hours. Solvent and excess thienyl chloride were removed by distillation under reduced pressure leaving trans 3-bromocinnamoyl chloride (12.2 g), b.p. 100°-100.5°C/0.2 mm Hg.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. customSolvent and excess thienyl chloride were removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-65e19e89e86746dfbf9dab08e8910bab
Source dataset
uspto-grants-1982_01
Patent number
US04309444

Reaction notes

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