Thionyl Chloride → 3-Fluoro-4-nitrobenzoyl chloride

HRID 880503

Reaction equation

HRID 880503 reaction equation
[F: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>>[F: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

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 2306533-Fluoro-4-nitrobenzoic acid

Product 1

HCID 27746563-Fluoro-4-nitrobenzoyl chlorideYield 99%

Procedure

A stirred solution of 3-fluoro-4-nitro-benzoic acid (1.65 g, 8.91 mmol) in thionyl chloride (10 mL) was heated at reflux for 2 h. Excess thionyl chloride was evaporated in vacuo and the residue azeotroped with toluene to afford 3-fluoro-4-nitro-benzoyl chloride (1.7 g, 99%) as a brown oil.

Workup

  1. temperatureat reflux for 2 h
  2. customExcess thionyl chloride was evaporated in vacuo
  3. customthe residue azeotroped with toluene

Sources & evidence

ORD record
ord-8da9e7ed9518459a824ff103d4a188b8
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Linked notes

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