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

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

Reactant 3

HCID 887Methanol

HCID 24758Sodium hydride

HCID 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.