Thionyl Chloride → 3-Chloro-4-nitrobenzoyl chloride

HRID 2234372Notes

Reaction equation

HRID 2234372 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5](O)=[O:6].S(Cl)([Cl:16])=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([Cl:16])=[O:6]

Participants

4

Reactant 2

HCID 24386Thionyl Chloride2×HCID 5209533-Chloro-4-nitrobenzoic acid

Product 1

HCID 190776143-Chloro-4-nitrobenzoyl chlorideYield 105.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-Chloro-4-nitrobenzoic acid (Apin; 1 g, 4.96 mmol) was suspended in toluene (10 mL) and thionyl chloride (1.11 mL, 14.88 mmol) added. The mixture was heated to 85° C. for 45 min Further thionyl chloride (1.1 mL) was added and the mixture heated at reflux. 0.5 hr. The reaction mixture was allowed to cool and stand overnight. The mixture was concentrated to give the title compound as a yellow liquid (1.15 g, 100%).

Workup

  1. additionwas added
  2. temperaturethe mixture heated
  3. temperatureat reflux
  4. custom0.5 hr
  5. temperatureto cool
  6. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-d4f1bf4d277b4b67b3b8551934dc57f5
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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