Thionyl Chloride → 2-Fluoro-3-nitrobenzoyl chloride

HRID 60090Notes

Reaction equation

HRID 60090 reaction equation
[F:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].S(Cl)([Cl:16])=O>CN(C)C=O>[F:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([Cl:16])=[O:5]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 186729922-Fluoro-3-nitrobenzoic acid

Product 1

HCID 510001272-Fluoro-3-nitrobenzoyl chlorideYield 98.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Conditions

Temperature
80 °C

Procedure

2-Fluoro-3-nitro-benzoic acid (16, 0.497 g, 2.68 mmol) is combined with thionyl chloride (3 mL, 40.0 mmol) and N,N-dimethylformamide (20 μL, 0.2 mmol) and the reaction is heated at 80° C. overnight. The reaction is concentrated under vacuum, suspended in toluene and concentrated under vacuum twice, and dried to provide the desired compound as a white solid (17, 0.535 g).

Workup

  1. concentrationThe reaction is concentrated under vacuum
  2. concentrationconcentrated under vacuum twice
  3. customdried

Sources & evidence

ORD record
ord-43d505b6b23147209b1e859579c13c54
Source dataset
uspto-grants-2016_09
Patent number
US09440969B2

Reaction notes

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