Oxalyl chloride → 1-Benzofuran-3-carbonyl chloride

HRID 1091313Notes

Reaction equation

HRID 1091313 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C:10]([OH:12])=O)=[CH:2]1.C(Cl)(=O)C([Cl:16])=O>C(Cl)Cl.CN(C=O)C>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C:10]([Cl:16])=[O:12])=[CH:2]1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 5956551-Benzofuran-3-carboxylic acid

Product 1

HCID 130247201-Benzofuran-3-carbonyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

Benzofuran-3-carboxylic acid (1.00 g, 6.17 mmol) was suspended in methylene chloride (20 mL), and oxalyl chloride (1.08 mL, 12.34 mmol) was added dropwise. To this reaction liquor, a catalytic amount of DMF (one drop) was added, and the reaction liquor was stirred for one hour at room temperature. The solvent was distilled off under reduced pressure, to obtain benzofuran-3-carboxylic acid chloride as a solid. The obtained acid chloride was suspended in 1,2-dichloroethane (20 mL), and (4-amino-3-chlorophenyl)acetic acid ethyl ester hydrochloride (1.54 g, 6.17 mmol) was added. The mixture was heated and stirred for 20 hours. The mixture was left to cool naturally to room temperature, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by flash column chromatography (Flash Chromatography System from Biotage AB, column size: 40S, elution solvent: n-hexane:ethyl acetate=95:5 to 75:25), to obtain the title compound (2.08 g, 94%) as a solid.

Workup

  1. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-7f96d38868b240759eace18d71b5f3ca
Source dataset
uspto-grants-2012_03
Patent number
US08129366B2

Reaction notes

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