Methanol → Methyl 5-fluoro-3-hydroxy-2-nitrobenzoate

HRID 249905Notes

Reaction equation

HRID 249905 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:14])[C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].S(Cl)(Cl)=O.[CH3:19]O>>[F:1][C:2]1[CH:3]=[C:4]([OH:14])[C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([O:9][CH3:19])=[O:8]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 668744845-Fluoro-3-hydroxy-2-nitrobenzoic acid

Product 1

HCID 66874176Methyl 5-fluoro-3-hydroxy-2-nitrobenzoateYield 41%

Conditions

Temperature
0 °C

Procedure

Crude 5-fluoro-3-hydroxy-2-nitrobenzoic acid (2.60 g, 12.92 mmol), was suspended in CH3OH (50 mL) and cooled to 0° C. Thionyl chloride (9.4 ml, 129.26 mmol) was added drop wise at 0° C. The mixture was allowed to warm to ambient temperature then heated to reflux for 17 h. The reaction mixture was allowed to cool to ambient temperature, and the solvent removed under reduced pressure. The crude material was purified by column chromatography (silica gel, 0 to 20% CH3OH in CH2Cl2) to afford methyl 5-fluoro-3-hydroxy-2-nitrobenzoate (1.15 g, 41%) as a white solid. 1H NMR and MS consistent.

Workup

  1. temperatureto warm to ambient temperature
  2. temperaturethen heated
  3. temperatureto reflux for 17 h
  4. temperatureto cool to ambient temperature
  5. customthe solvent removed under reduced pressure
  6. customThe crude material was purified by column chromatography (silica gel, 0 to 20% CH3OH in CH2Cl2)

Sources & evidence

ORD record
ord-2508e657932b4b1b96523fef6da676f0
Source dataset
uspto-grants-2011_01
Patent number
US07863271B2

Reaction notes

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