Methanol → Methyl 2-fluoro-4-nitrobenzoate

HRID 1843033Notes

Reaction equation

HRID 1843033 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]([OH:6])=[O:5].OS(O)(=O)=O.[CH3:19]O>>[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:6][CH3:19])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 3026792-Fluoro-4-nitrobenzoic acid

Product 1

HCID 3013872Methyl 2-fluoro-4-nitrobenzoateYield 98%

Procedure

To a solution of 2-fluoro-4-nitrobenzoic acid (1 g, 5.402 mmol) in MeOH was added H2SO4 (2.9 ml). The reaction mixture was refluxed overnight, and then cooled to room temperature and concentrated. The residue was diluted with EtOAc and washed with a saturated NaHCO3 solution. The organic layer was dried over MgSO4 and concentrated. The crude product was purified by column chromatography to afford the pure compound methyl 2-fluoro-4-nitrobenzoate (1.05 g, 98%).

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. concentrationconcentrated
  3. additionThe residue was diluted with EtOAc
  4. washwashed with a saturated NaHCO3 solution
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-d0ad11d845b44ef28d368ae79c14eddd
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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