Thionyl Chloride → 5-Bromothiophene-2-carbonyl chloride

HRID 871982Notes

Reaction equation

HRID 871982 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]([OH:9])=O)=[CH:4][CH:3]=1.S(Cl)([Cl:12])=O>CN(C)C=O.C(Cl)(Cl)Cl>[Br:1][C:2]1[S:6][C:5]([C:7]([Cl:12])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 3491155-Bromothiophene-2-carboxylic acid

Product 1

HCID 6057125-Bromothiophene-2-carbonyl chlorideYield 99.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6212ChloroformSolvent

Procedure

A mixture of 5-bromothiophene-2-carboxylic acid (300 mg, 1.45 mmol), thionyl chloride (423 μL, 5.80 mmol), and N,N-dimethylformamide (1 drop) was dissolved in chloroform (3 mL), and refluxed for 1 hour. After cooling down, the reaction mixture was concentrated under reduced pressure to give the titled reference compound (324 mg) as a pale yellow solid. (Yield 99%)

Workup

  1. temperaturerefluxed for 1 hour
  2. temperatureAfter cooling down
  3. concentrationthe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d0ce89272be544318855abbabb7461bd
Source dataset
uspto-grants-2015_03
Patent number
US08975256B2

Reaction notes

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