Ethanol → Ethyl 5-bromothiophene-3-carboxylate

HRID 720233Notes

Reaction equation

HRID 720233 reaction equation
[Br:1][C:2]1[S:6][CH:5]=[C:4]([C:7]([OH:9])=[O:8])[CH:3]=1.[CH3:10][CH2:11]O>O=S(Cl)Cl>[CH2:10]([O:8][C:7]([C:4]1[CH:3]=[C:2]([Br:1])[S:6][CH:5]=1)=[O:9])[CH3:11]

Participants

4

Reactant 2

HCID 702EthanolHCID 120399785-Bromothiophene-3-carboxylic acid

Product 1

HCID 15293216Ethyl 5-bromothiophene-3-carboxylate

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

A solution of 5-bromo-thiophene-3-carboxylic acid (14.5 g, 70 mmol) was dissolved in SOCl2 and the mixture was refluxed for 2 hours. The mixture was concentrated under reduced pressure to give a yellow oil. The oil was was dissolved in EtOH and the mixture was refluxed for 1 hour, then concentrated under reduced pressure to give 5-bromo-thiophene-3-carboxylic acid ethyl ester as an oil (16.46 g, quantitative).

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customto give a yellow oil
  4. temperaturethe mixture was refluxed for 1 hour
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8fe7d8003aec45f59672936f8ac77628
Source dataset
uspto-grants-2006_11
Patent number
US07135470B2

Reaction notes

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