Oxalyl chloride → 2-Chloro-4-fluoro-5-nitrobenzoyl chloride

HRID 277369Notes

Reaction equation

HRID 277369 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:3]=1[C:4](O)=[O:5].C(Cl)(=O)C([Cl:18])=O>CN(C)C=O.ClCCCl>[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:3]=1[C:4]([Cl:18])=[O:5]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 72108282-Chloro-4-fluoro-5-nitrobenzoic Acid

Product 1

HCID 151243842-Chloro-4-fluoro-5-nitrobenzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 2-chloro-4-fluoro-5-nitrobenzoic acid (50.0 g, 0.228 mol) and N,N-dimethylformamide (5 drops) in 1,2-dichloroethane is treated dropwise with oxalyl chloride (30.8 mL, 0.353 mol), refluxed for 3 hours, cooled, and concentrated in vacuo to obtain the title product as an orange solid which is identified by NMR spectral analyses.

Workup

  1. temperaturerefluxed for 3 hours
  2. temperaturecooled
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-022def1681e94c3f87923f294e8f357d
Source dataset
uspto-grants-2002_03
Patent number
US06355796B1

Reaction notes

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