Oxalyl chloride → 3-Fluoro-6-trifluoromethyl-benzo[b]thiophene-2-carbonyl chloride

HRID 409906Notes

Reaction equation

HRID 409906 reaction equation
[F:1][C:2]1[C:3]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][C:4]=2[S:5][C:6]=1[C:7](O)=[O:8].C(Cl)(C([Cl:22])=O)=O>C(Cl)Cl.CN(C=O)C>[F:1][C:2]1[C:3]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][C:4]=2[S:5][C:6]=1[C:7]([Cl:22])=[O:8]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 596258883-Fluoro-6-trifluoromethyl-benzo[b]thiophene-2-carboxylic acid

Product 1

HCID 596256893-Fluoro-6-trifluoromethyl-benzo[b]thiophene-2-carbonyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To compound 15b (0.14 g, 0.53 mmol) in CH2Cl2 (5 mL) at room temperature was added (COCl)2 (0.051 mL, 0.58 mmol), followed by 2 drops of DMF. The reaction mixture was stirred at room temperature for 18 h. The reaction mixture was then concentrated to give compound 15c.

Workup

  1. concentrationThe reaction mixture was then concentrated

Sources & evidence

ORD record
ord-bfba03d71a0142229485b23ba6691927
Source dataset
uspto-grants-2014_06
Patent number
US08759533B2

Reaction notes

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