Oxalyl chloride → 4-Fluoro-2-(trifluoromethyl)benzoyl chloride

HRID 1978177Notes

Reaction equation

HRID 1978177 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:11]=[C:10]([F:12])[CH:9]=[CH:8][C:4]=1[C:5](O)=[O:6].C(Cl)(=O)C([Cl:18])=O>ClCCl.CN(C)C=O>[F:1][C:2]([F:14])([F:13])[C:3]1[CH:11]=[C:10]([F:12])[CH:9]=[CH:8][C:4]=1[C:5]([Cl:18])=[O:6]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 6882554-Fluoro-2-(trifluoromethyl)benzoic acid

Product 1

HCID 6056804-Fluoro-2-(trifluoromethyl)benzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A suspension of 2-trifluoromethyl-4-fluorobenzoic acid (16.85 g, 81 mmol) in dichloromethane (150 mL) containing a few drops of dimethylformamide was treated dropwise under nitrogen with oxalyl chloride (8.5 mL, 97.4 mmol). After the gas evolution subsided, the reaction mixture was refluxed for an additional 10 minutes, and then evaporated to dryness in vacuo. The crude acid chloride was used as such in the next step.

Workup

  1. temperaturethe reaction mixture was refluxed for an additional 10 minutes
  2. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-f1f786b53c1e443ba771a2b5f71fdd54
Source dataset
uspto-grants-2001_05
Patent number
US06235900B1

Reaction notes

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