Thionyl Chloride → 2-Fluoro-4-nitrobenzoyl chloride

HRID 2234503Notes

Reaction equation

HRID 2234503 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].S(Cl)([Cl:16])=O>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([Cl:16])=[O:5]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 3026792-Fluoro-4-nitrobenzoic acid

Product 1

HCID 104204352-Fluoro-4-nitrobenzoyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-fluoro-4-nitrobenzoic acid (Fluorochem; 2.5 g, 13.51 mmol) was suspended in toluene (25 mL) and thionyl chloride (2.96 mL, 40.52 mmol) added. The reaction mixture was heated at reflux for 1.5 hours, allowed to cool and evaporated to give the title compound as a yellow liquid which gradually solidified on standing (2.74 g, 100%)

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 1.5 hours
  3. temperatureto cool
  4. customevaporated

Sources & evidence

ORD record
ord-3c2182da636d41988dee6ad1f67d54c6
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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