Oxalyl chloride → 5-Bromo-2-fluorobenzoyl chloride

HRID 659878Notes

Reaction equation

HRID 659878 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[Br:7][C:8]1[CH:9]=C[C:11]([F:17])=[C:12]([CH:16]=1)C(O)=O>ClCCl.CN(C)C=O>[Br:7][C:8]1[CH:16]=[CH:12][C:11]([F:17])=[C:1]([CH:9]=1)[C:2]([Cl:4])=[O:3]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 27363155-Bromo-2-fluorobenzoic acid

Product 1

HCID 219426655-Bromo-2-fluorobenzoyl chlorideYield 99.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (11.0 mL, 126 mmol) was added dropwise to a well stirred suspension of 5-bromo-2-fluoro-benzoic acid (25.0 g, 114 mmol) in dichloromethane (150 mL) and N,N-dimethylformamide (1.5 mL) at 0° C. The resulting mixture was allowed to gradually warm to room temperature. After 18 hours, the solid had gone into solution. The resulting light orange solution was concentrated under reduced pressure and was chased two times with diethyl ether to afford 5-bromo-2-fluoro-benzoyl chloride (27.0 g, quantitative yield) as a pale orange oil.

Workup

  1. concentrationThe resulting light orange solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3b5625de08e74deebdad7445de2bad4a
Source dataset
uspto-grants-2011_12
Patent number
US08080580B2

Reaction notes

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