Benzofuran-2-carboxylic acid → 2-Benzofurancarbonyl chloride

HRID 432470Notes

Reaction equation

HRID 432470 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([OH:12])=O.C(Cl)(=O)C([Cl:16])=O>ClCCl.CN(C)C=O>[O:1]1[C:2]([C:10]([Cl:16])=[O:12])=[CH:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]1=2

Participants

5

Reactant 2

HCID 10331Benzofuran-2-carboxylic acidHCID 65578Oxalyl chloride

Product 1

HCID 389492-Benzofurancarbonyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A suspension of 2-benzofurancarboxylic acid (0.746 g, 4.6 mmol) in dichloromethane (3 mL) was treated with oxalyl chloride (0.700 g, 5.52 mmol) and one drop of dimethylformamide. The reaction mixture was shaken for 15 h. The solvent was removed under reduced pressure and dried under high vacuum to afford a quantitative amount of benzo[b]furan-2-carbonyl chloride. The oil was directly used in the following reaction.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customdried under high vacuum

Sources & evidence

ORD record
ord-382df506ee9f40868a48b36b0e64e20c
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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