Dimethylformamide → 3-bromo-5-fluorobenzoyl chloride

HRID 1496992Notes

Reaction equation

HRID 1496992 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([F:11])[CH:10]=1)[C:5](O)=[O:6].CN(C=O)C.C(Cl)(=O)C([Cl:20])=O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([F:11])[CH:10]=1)[C:5]([Cl:20])=[O:6]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 27733393-Bromo-5-fluorobenzoic acid

Product 1

HCID 27833453-bromo-5-fluorobenzoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10 g of 3-bromo-5-fluoro-benzoic acid are suspended in 100 ml of DCM, 0.5 ml DMF and 4.5 ml oxalyl chloride (1.15 Eq) are added and the resulting mixture is stirred for 100 minutes at RT. The solvent is removed by vacuo and the benzoic acid chloride is isolated by distillation.

Workup

  1. customThe solvent is removed by vacuo

Sources & evidence

ORD record
ord-66fa69f971064cbe863bd8e0e91ff497
Source dataset
uspto-grants-2015_12
Patent number
US09199947B2

Reaction notes

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