Methanol → Methyl 3-fluoro-4-nitrobenzoate

HRID 18482

Reaction equation

HRID 18482 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]([OH:7])=[O:6].[CH3:14]O>>[CH3:14][O:6][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][C:10]([N+:11]([O-:13])=[O:12])=[C:2]([F:1])[CH:3]=1

Participants

3

Reactant 2

HCID 887MethanolHCID 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 5H2SO4 (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-536115a2a5e24beb829c5c8865d8c9cb
Source dataset
uspto-grants-2010_06
Patent number
US07741355B2

Linked notes

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