Methanol → Methyl 4-fluoro-3-nitrobenzoate

HRID 2205095Notes

Reaction equation

HRID 2205095 reaction equation
S(Cl)(Cl)=O.[F:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][C:7]=1[N+:15]([O-:17])=[O:16].[CH3:18]O>>[F:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([O:12][CH3:18])=[O:11])=[CH:8][C:7]=1[N+:15]([O-:17])=[O:16]

Participants

4

Reactant 3

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

Product 1

HCID 5219721Methyl 4-fluoro-3-nitrobenzoate

Procedure

Thionyl chloride (24 g, 201.68 mmol, 1.01 equiv) was added dropwise with stirring at 0° C. to a solution of 4-fluoro-3-nitrobenzoic acid (37 g, 200.00 mmol, 1.00 equiv) in MeOH (400 mL) and allowed to react, with stifling, for 3 hrs under reflux. The resulting mixture was concentrated under vacuum, diluted with 500 mL of EA, and washed with 3×200 mL of saturated NaHCO3 and 1×200 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum affording 40 g (crude) of methyl 4-fluoro-3-nitrobenzoate as a white solid.

Workup

  1. customto react
  2. temperatureunder reflux
  3. concentrationThe resulting mixture was concentrated under vacuum
  4. additiondiluted with 500 mL of EA
  5. washwashed with 3×200 mL of saturated NaHCO3 and 1×200 mL of brine
  6. dry with materialThe mixture was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-6ae03130fb5d4f87817ba62a79f47a58
Source dataset
uspto-grants-2016_06
Patent number
US09370522B2

Reaction notes

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