Oxalyl chloride → Methyl 4-fluoro-3-nitrobenzoate

HRID 2244016Notes

Reaction equation

HRID 2244016 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[C:14](Cl)(=O)C(Cl)=O>CO>[CH3:14][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([F:1])=[C:3]([N+:11]([O-:13])=[O:12])[CH:4]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 679874-Fluoro-3-nitrobenzoic acid

Product 1

HCID 5219721Methyl 4-fluoro-3-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Heat a solution of 4-fluoro-3-nitro-benzoic acid (5.00 g, 27.0 mmol, Sigma Chemical Co.) in methanol (135 mL, 0.2M) at reflux and slowly add oxalyl chloride (6.86 g, 54.0 mmol, Aldrich Chemical Co.) through reflux condenser. Stir for 2 h at reflux. Concentrate reaction mixture in vacuo. The title compound solidifies upon standing (5.30 g, 26.6 mmol, 99%): 19F NMR (acetone-d6, 400 MHz) δ-121.3.

Workup

  1. temperatureat reflux
  2. temperatureat reflux
  3. concentrationConcentrate
  4. customreaction mixture in vacuo

Sources & evidence

ORD record
ord-8a92caef84bb4f19b144a4f9f57f8daf
Source dataset
uspto-grants-2010_03
Patent number
US07678794B2

Reaction notes

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