Dimethylformamide → 4-(4-Chloro-2-nitrophenoxy)benzoyl chloride

HRID 2197846Notes

Reaction equation

HRID 2197846 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:15]=[CH:14][C:10]([C:11](O)=[O:12])=[CH:9][CH:8]=2)=[C:4]([N+:18]([O-:20])=[O:19])[CH:3]=1.C(Cl)(=O)C([Cl:24])=O.CN(C=O)C>C(Cl)Cl>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:15]=[CH:14][C:10]([C:11]([Cl:24])=[O:12])=[CH:9][CH:8]=2)=[C:4]([N+:18]([O-:20])=[O:19])[CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 24422524-(4-Chloro-2-nitrophenoxy)benzoic acid

Product 1

HCID 866154944-(4-Chloro-2-nitrophenoxy)benzoyl chlorideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product from Example 126b (4.0 g, 13.6 mmol) in 40 mL of CH2Cl2 was treated with oxalyl chloride (3.5 g, 27.2 mmol) and DMF (catalytic amount). Mixture was stirred for 12 hours. Mixture was concentrated under vacuum giving the title compound as a yellow oil (4.2 g, 100%).

Workup

  1. concentrationMixture was concentrated under vacuum

Sources & evidence

ORD record
ord-d55f472e4277449bbe57b36f047272f7
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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