Methanol → Methyl 3-fluoro-4-nitrobenzoate

HRID 501464Notes

Reaction equation

HRID 501464 reaction equation
OS(O)(=O)=O.[F:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=1[N+:16]([O-:18])=[O:17])[C:10]([OH:12])=[O:11].[CH3:19]O>>[CH3:19][O:11][C:10](=[O:12])[C:9]1[CH:13]=[CH:14][C:15]([N+:16]([O-:18])=[O:17])=[C:7]([F:6])[CH:8]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 2306533-Fluoro-4-nitrobenzoic acid

Product 1

HCID 592761Methyl 3-fluoro-4-nitrobenzoate

Procedure

A 1 L round bottom flask equipped with a stir bar and reflux condenser was charged H2SO4 (4 mL), methanol (400 mL) and 3-fluoro-4-nitrobenzoic acid (10 g). The reaction mixture was heated at reflux temperatures with vigorous stirring for 18 h. The methanol was removed and the crude residue was triturated with hexane and concentrated to give a colorless solid (9.79 g) that was used without further purification.

Workup

  1. customA 1 L round bottom flask equipped with a stir bar
  2. temperaturereflux condenser
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux temperatures
  5. customThe methanol was removed
  6. customthe crude residue was triturated with hexane
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3991e9a749fa4c5d9579ea3a8d74c584
Source dataset
uspto-grants-2010_08
Patent number
US07772266B2

Reaction notes

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