Methanol → Methyl 4-fluoro-3-nitrobenzoate

HRID 1916289Notes

Reaction equation

HRID 1916289 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].S(=O)(=O)(O)O.[CH3:19]O>>[CH3:19][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 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 679874-Fluoro-3-nitrobenzoic acid

Product 1

HCID 5219721Methyl 4-fluoro-3-nitrobenzoate

Procedure

To a solution of 4-fluoro-3-nitro-benzoic acid (5.05 g, 27 mmol) in 50 mL methanol was added 1 mL of 99% sulphuric acid. The mixture was refluxed overnight, allowed to cool and then concentrated in vacuo. The resulting residue was dissolved in ethyl acetate and washed with saturated sodium bicarbonate solution. The organic layer was then dried over sodium sulphate and concentrated in vacuo to give the title product as a white solid (5.15 g, 26 mmol). 1H NMR (DMSO) δ 8.50 (1H, d), 8.30-8.27 (1H, m), 7.71 (1H, t), 3.90 (3H, s); LC-MS Rt 1.93 min.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. temperatureto cool
  3. concentrationconcentrated in vacuo
  4. dissolutionThe resulting residue was dissolved in ethyl acetate
  5. washwashed with saturated sodium bicarbonate solution
  6. dry with materialThe organic layer was then dried over sodium sulphate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a09802aeb42b4007a79ab3c5635c1664
Source dataset
uspto-grants-2013_12
Patent number
US08618121B2

Reaction notes

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