Oxalyl chloride → 5-Chlorothiophene-2-carbonyl Chloride

HRID 2194376Notes

Reaction equation

HRID 2194376 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([OH:9])=O)=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:13])=O>ClCCl>[Cl:1][C:2]1[S:6][C:5]([C:7]([Cl:13])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 950485-Chloro-2-thiophenecarboxylic acid

Product 1

HCID 5892235-Chlorothiophene-2-carbonyl Chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

480 mg (2.95 mmol) of 5-chlorothiophene-2-carboxylic acid are dissolved in 24 ml of dichloromethane, and 2.4 ml (27.5 mmol) of oxalyl chloride are added. The mixture is heated under reflux for 16 h. It is then concentrated in vacuo, and the residue is again mixed with dichloromethane and concentrated once again. A viscous oil remains and is dried under high vacuum. 534 mg (quant.) of the target compound are obtained and are reacted further without further purification and characterization.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 16 h
  3. concentrationIt is then concentrated in vacuo
  4. additionthe residue is again mixed with dichloromethane
  5. concentrationconcentrated once again
  6. customA viscous oil remains and is dried under high vacuum
  7. custom534 mg (quant.) of the target compound are obtained
  8. customare reacted further without further purification and characterization

Sources & evidence

ORD record
ord-7570e48ba1324aabbf32e64af8e5cec4
Source dataset
uspto-grants-2012_12
Patent number
US08334284B2

Reaction notes

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