Methanol → Methyl 4-fluoro-2-nitrobenzoate

HRID 1385304Notes

Reaction equation

HRID 1385304 reaction equation
S(Cl)(Cl)=O.[F:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[C:8]([N+:15]([O-:17])=[O:16])[CH:7]=1.[CH3:18]O>>[F:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([O:12][CH3:18])=[O:11])=[C:8]([N+:15]([O-:17])=[O:16])[CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 27374164-Fluoro-2-nitrobenzoic acid

Product 1

HCID 14941412Methyl 4-fluoro-2-nitrobenzoate

Procedure

Thionyl chloride (31.5 ml; 0.432 mol) was slowly added dropwise at 0C to a solution of 4-fluoro-2-nitrobenzoic acid (16.0 g, 86.4 mmol) in methanol (240 ml). After warming to RT, stirring overnight and boiling under reflux for 4 h, the reaction solution was concentrated in vacuo and partitioned between ethyl acetate and potassium hydrogencarbonate solution. Drying and concentration of the organic phase afforded a yellow oil.

Workup

  1. temperatureunder reflux for 4 h
  2. concentrationthe reaction solution was concentrated in vacuo
  3. custompartitioned between ethyl acetate and potassium hydrogencarbonate solution
  4. customDrying
  5. customconcentration of the organic phase afforded a yellow oil

Sources & evidence

ORD record
ord-ac0c3137642540c3ac0e1304f6db402f
Source dataset
uspto-grants-2001_07
Patent number
US06262112B1

Reaction notes

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