Methanol → Methyl 4-fluoro-3-nitrobenzoate

HRID 1038527Notes

Reaction equation

HRID 1038527 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[F:13])[C:7]([OH:9])=[O:8])([O-:3])=[O:2].S(Cl)(Cl)=O.[CH3:18]O>>[F:13][C:12]1[CH:11]=[CH:10][C:6]([C:7]([O:9][CH3:18])=[O:8])=[CH:5][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

4

Reactant 3

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

Product 1

HCID 5219721Methyl 4-fluoro-3-nitrobenzoateYield 99%

Conditions

Temperature
-78 °C

Procedure

3-Nitro-4-fluorobenzoic acid (25.6 g, 138 mmol) was dissolved in methanol (300 mL), added thionyl chloride (18.4 mL, 258 mmol) under −78° C. The mixture was stirred at −78° C. for 10 minutes, and then stirred at room temperature overnight. The reaction solution was concentrated in vacuo. The obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate). The title compound (29.6 g (yield >99%)) was obtained as a white crystal.

Workup

  1. stirringstirred at room temperature overnight
  2. concentrationThe reaction solution was concentrated in vacuo
  3. customThe obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-30e03b0647314d199256a512d8442c89
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Reaction notes

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