Oxalyl chloride → 2-Chloro-4-fluorobenzoyl chloride

HRID 1978171Notes

Reaction equation

HRID 1978171 reaction equation
[Cl: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>[Cl: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 752592-Chloro-4-fluorobenzoic acid

Product 1

HCID 27365462-Chloro-4-fluorobenzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A suspension of the 2-chloro-4-fluorobenzoic acid (13.61 g, 78 mmol) in dichloromethane (85 mL) containing a few drops of dimethylformamide was treated dropwise under nitrogen with a 2M solution of oxalyl chloride in dichloromethane (1.2 equivalents). After gas evolution subsided, the reaction mixture was refluxed for an additional 25 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 25 minutes
  2. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-104879018de9438eb6ab4391630114e3
Source dataset
uspto-grants-2001_05
Patent number
US06235900B1

Reaction notes

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