4-Chloro-3-nitrobenzoic acid → 4-Chloro-3-nitrobenzoyl chloride

HRID 1280078Notes

Reaction equation

HRID 1280078 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].C(Cl)(=O)C([Cl:17])=O>C(Cl)Cl.CN(C=O)C>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([Cl:17])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

5

Reactant 2

HCID 73204-Chloro-3-nitrobenzoic acidHCID 65578Oxalyl chloride

Product 1

HCID 1234774-Chloro-3-nitrobenzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

4-Chloro-3-nitrobenzoic acid (40.40 g, 0.20 mole) was suspended in DCM (100 mL) containing 3 drops of DMF. Oxalyl chloride (1.5 equivalents, 0.3 mole, 27 mL) was added in small portions and the mixture stirred overnight at room temperature. After refluxing for an additional hour to complete the reaction, volatiles were removed under reduced pressure and the residue was coevaporated twice with hexane to give the title compound as a light yellow solid.

Workup

  1. temperatureAfter refluxing for an additional hour
  2. customthe reaction, volatiles
  3. customwere removed under reduced pressure

Sources & evidence

ORD record
ord-111dcc6f0567425693a97f36221f1c21
Source dataset
uspto-grants-2002_09
Patent number
US06448281B1

Reaction notes

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