Dichloromethane → 2,4-Difluoro-5-nitrobenzoyl chloride

HRID 369610Notes

Reaction equation

HRID 369610 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[F:7][C:8]1[CH:16]=[C:15]([F:17])[C:14]([N+:18]([O-:20])=[O:19])=[CH:13]C=1C(O)=O.C(Cl)Cl>CN(C)C=O>[F:7][C:8]1[CH:16]=[C:15]([F:17])[C:14]([N+:18]([O-:20])=[O:19])=[CH:13][C:1]=1[C:2]([Cl:4])=[O:3]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 27828222,4-Difluoro-5-nitrobenzoic acid

Product 1

HCID 183144972,4-Difluoro-5-nitrobenzoyl chlorideYield 101.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Oxalyl chloride (94.0 g, 0.739 mol) is added dropwise to a mixture of 2,4-difluoro-5-nitrobenzoic acid (100.0 g, 0.492 mol), methylene chloride and N,N-dimethylformamide (0.600 ml). The resultant mixture is stirred 3.25 hours at reflux, cooled to room temperature, and concentrated in vacuo to afford the title compound as a brown oil (111 g, 95.2%).

Workup

  1. temperatureat reflux
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-375256ce718441e094289e1819a265c1
Source dataset
uspto-grants-2000_10
Patent number
US06140270

Reaction notes

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