Oxalyl chloride → 6-(Trifluoromethyl)benzo[b]thiophene-2-carbonyl chloride

HRID 409891Notes

Reaction equation

HRID 409891 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[CH:5][C:6]2[CH:10]=[C:9]([C:11](O)=[O:12])[S:8][C:7]=2[CH:14]=1.C(Cl)(C([Cl:21])=O)=O>C(Cl)Cl.CN(C=O)C>[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[CH:5][C:6]2[CH:10]=[C:9]([C:11]([Cl:21])=[O:12])[S:8][C:7]=2[CH:14]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 179795236-(Trifluoromethyl)benzo[b]thiophene-2-carboxylic acid

Product 1

HCID 577187896-(Trifluoromethyl)benzo[b]thiophene-2-carbonyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 6-(trifluoromethyl)benzo[b]thiophene-2-carboxylic acid 4a (65 mg, 0.26 mmol) in CH2Cl2 (2.5 mL) was added (COCl)2 (0.026 mL, 0.30 mmol), followed by DMF (1 drop) at room temperature. The reaction was kept at room temperature for 20 h. The resulting solution was concentrated to give compound 4b.

Workup

  1. concentrationThe resulting solution was concentrated

Sources & evidence

ORD record
ord-d8b18ac9511a4acb98d4a2af7aa2bb92
Source dataset
uspto-grants-2014_06
Patent number
US08759533B2

Reaction notes

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