Methanol → Methyl 2-fluoro-5-methoxy-4-nitrobenzoate

HRID 1676528Notes

Reaction equation

HRID 1676528 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5](=[O:17])[C:6]1[CH:11]=[C:10](F)[C:9]([N+:13]([O-:15])=[O:14])=[CH:8][C:7]=1[F:16].[CH3:18][OH:19]>>[CH3:3][O:4][C:5](=[O:17])[C:6]1[CH:11]=[C:10]([O:19][CH3:18])[C:9]([N+:13]([O-:15])=[O:14])=[CH:8][C:7]=1[F:16]

Participants

4

Reactant 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 18526058Methyl 2,5-difluoro-4-nitrobenzoate

Product 1

HCID 67076410Methyl 2-fluoro-5-methoxy-4-nitrobenzoate

Procedure

To a mixture 0.30 g (7.55 mmole) of sodium hydride (60% in mineral oil) and 30 mL of methanol was added 1.49 g (6.86 mmole) of 2,5-difluoro-4-nitro-benzoic acid methyl ester. The mixture was heated at reflux for 18 hours and then quenched by the addition of water, and then concentrated under reduced pressure. The residue was diluted with ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with dichloromethane-hexanes (1:1) to give 0.92 g of 2-fluoro-5-methoxy-4-nitro-benzoic acid methyl ester.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 18 hours
  3. customquenched by the addition of water
  4. concentrationconcentrated under reduced pressure
  5. additionThe residue was diluted with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel chromatography
  11. washeluting with dichloromethane-hexanes (1:1)

Sources & evidence

ORD record
ord-03bd0a727f06419e82acd7e013d70357
Source dataset
uspto-grants-2011_08
Patent number
US08003785B2

Reaction notes

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