Methanol → Methyl 4-fluoro-3-nitrobenzoate

HRID 2407346Notes

Reaction equation

HRID 2407346 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(Cl)(Cl)=O.[CH3:18]O>>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:18])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 679874-Fluoro-3-nitrobenzoic acid

Product 1

HCID 5219721Methyl 4-fluoro-3-nitrobenzoateYield 97%

Procedure

4-Fluoro-3-nitrobenzoic acid (3.00 g, 16.2 mmol) was dissolved in methanol 40 mL, and thionyl chloride (3.5 mL, 48.6 mmol) was slowly added thereto at 0° C. The temperature was slowly raised to room temperature, and then stirred under reflux for 1 hour. The solvent was removed by concentration under reduced pressure, to obtain a target compound as an ivory solid (3.12 g, 97%).

Workup

  1. customat 0° C
  2. temperatureunder reflux for 1 hour
  3. customThe solvent was removed by concentration under reduced pressure

Sources & evidence

ORD record
ord-af453165d99a43dd8db0c97f07d835af
Source dataset
uspto-grants-2014_08
Patent number
US08809541B2

Reaction notes

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