Benzene → HCID 21708268, compound

HRID 1458211Notes

Reaction equation

HRID 1458211 reaction equation
S(Cl)([Cl:3])=O.C1C=CC=CC=1.[Cl:11][C:12]1[C:20]([Br:21])=[CH:19][C:18]([N+:22]([O-:24])=[O:23])=[CH:17][C:13]=1[C:14](O)=[O:15]>CN(C=O)C>[Cl:11][C:12]1[C:20]([Br:21])=[CH:19][C:18]([N+:22]([O-:24])=[O:23])=[CH:17][C:13]=1[C:14]([Cl:3])=[O:15]

Participants

5

Reactant 3

HCID 241BenzeneHCID 24386Thionyl ChlorideHCID 21708228HCID 21708228, compound

Product 1

HCID 21708268HCID 21708268, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.1 ml (69.9 mmol) of thionyl chloride and a solvent mixture comprising 50 ml of benzene and 0.2 ml of DMF were added to 14.07 g (50.2 mmol) of 2-chloro-3-bromo-5-nitrobenzoic acid. The obtained mixture was heated under reflux for 2 hours and distilled to remove the solvent. Benzene was added to the residue and the obtained mixture was distilled again to remove the solvent. Thus, 15.07 g of the title compound was obtained (yield: quantitative).

Workup

  1. temperatureThe obtained mixture was heated
  2. temperatureunder reflux for 2 hours
  3. distillationdistilled
  4. customto remove the solvent
  5. additionBenzene was added to the residue
  6. distillationthe obtained mixture was distilled again
  7. customto remove the solvent

Sources & evidence

ORD record
ord-b6e7dce809ea4138820e7b572d80f9d6
Source dataset
uspto-grants-1998_12
Patent number
US05849912

Reaction notes

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