Oxalyl chloride → 2,4-Difluorobenzoyl chloride

HRID 1978185Notes

Reaction equation

HRID 1978185 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].C(Cl)(=O)C([Cl:15])=O>ClCCl.CN(C)C=O>[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4]([Cl:15])=[O:5]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 741022,4-Difluorobenzoic acid

Product 1

HCID 5880812,4-Difluorobenzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A suspension of 2,4-difluorobenzoic acid (3.6 g, 22.8 mmol) in dichloromethane (40 mL) containing a few drops of dimethylformamide was treated dropwise under nitrogen with oxalyl chloride (2.4 mL, 27.5 mmol). After gas evolution subsided, the reaction mixture was refluxed for an additional 15 minutes, and then the solution was 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 15 minutes
  2. customthe solution was evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-453f10d234b04894b834619386d92ae9
Source dataset
uspto-grants-2001_05
Patent number
US06235900B1

Reaction notes

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