Oxalyl chloride → 2-Bromo-4-fluorobenzoyl chloride

HRID 1978174Notes

Reaction equation

HRID 1978174 reaction equation
[Br: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>[Br: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 12681692-Bromo-4-fluorobenzoic acid

Product 1

HCID 27833462-Bromo-4-fluorobenzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A suspension of 2-bromo-4-fluorobenzoic acid (6.87 g, 31.37 mmol) in dichloromethane (70 mL) containing a few drops of dimethylformamide was treated dropwise under nitrogen with a 2M solution of oxalyl chloride in dichloromethane (1.16 equivalents). After gas evolution subsided, the reaction mixture was refluxed for an additional 25 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 25 minutes
  2. customthe solution was evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-7e538be280b74d5da04b092050af457f
Source dataset
uspto-grants-2001_05
Patent number
US06235900B1

Reaction notes

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