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

HRID 1007695Notes

Reaction equation

HRID 1007695 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-fbed5f00cdd74de0b0691d5cb1b66224
Source dataset
uspto-grants-2004_09
Patent number
US06794404B2

Reaction notes

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