Thionyl Chloride → 2-Bromothiophene-3-carbonyl chloride

HRID 445215Notes

Reaction equation

HRID 445215 reaction equation
S(Cl)([Cl:3])=O.[Br:5][C:6]1[S:7][CH:8]=[CH:9][C:10]=1[C:11]([OH:13])=O>C1(C)C=CC=CC=1>[Br:5][C:6]1[S:7][CH:8]=[CH:9][C:10]=1[C:11]([Cl:3])=[O:13]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 123209712-Bromothiophene-3-carboxylic acid

Product 1

HCID 201947092-Bromothiophene-3-carbonyl chlorideYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Add thionyl chloride (0.35 mL, 4.80 mmol) to a solution of 2-bromothiophene-3-carboxylic acid (500 mg, 2.41 mmol) and toluene (20 mL) with stirring. Purge the reaction vessel with nitrogen. Heat the mixture to reflux and stir for 3 hours. Concentrate the mixture to obtain the title compound (540 mg, 2.41 mmol). Use compound in next procedure without further purification.

Workup

  1. customPurge the reaction vessel with nitrogen
  2. temperatureHeat the mixture
  3. temperatureto reflux
  4. stirringstir for 3 hours
  5. concentrationConcentrate the mixture

Sources & evidence

ORD record
ord-458724e3d972488db0d8cb6cf56d7581
Source dataset
uspto-grants-2013_07
Patent number
US08476300B2

Reaction notes

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