Oxalyl chloride → 5-Chlorothiophene-2-carbonyl Chloride

HRID 1437534Notes

Reaction equation

HRID 1437534 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>CCOC(C)=O.CN(C=O)C>[Cl:1][C:2]1[S:6][C:5]([C:7]([Cl:13])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

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

Product 1

HCID 5892235-Chlorothiophene-2-carbonyl Chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a chilled solution of 5-chlorothiophene-2-carboxylic acid (0.16 g, 1.0 mmol) in EtOAc (3 mL) and DMF (1 drop) was added neat oxalyl chloride (92 μL, 1.05 mmol). The reaction mixture was stirred cold for 2 hr and concentrated in vacuo to give crude 5-chlorothiophene-2-carbonyl chloride.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-591722fd2a364b0896214ea572f7007f
Source dataset
uspto-grants-2009_11
Patent number
US07622474B2

Reaction notes

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