Potassium Nitrate → 2-Fluoro-5-methoxycarbonyloxy-4-methylnitrobenzene

HRID 2060685Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:13])[O:4][C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=1[CH3:12].[N+:14]([O-])([O-:16])=[O:15].[K+]>S(=O)(=O)(O)O>[CH3:1][O:2][C:3](=[O:13])[O:4][C:5]1[CH:10]=[C:9]([N+:14]([O-:16])=[O:15])[C:8]([F:11])=[CH:7][C:6]=1[CH3:12]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of carbonic acid 4-fluoro-2-methyl-phenyl ester methyl ester (15 g, 81.5 mmol) in conc. sulfuric acid (100 mL) at 0° C. was added powdered KNO3 (8.3 g, 82.2 mmol) in several portions. The reaction mixture was stirred for 1 hour at 0° C. and was then poured into ice water and extracted with ethyl acetate (3×100 mL). The extracts were washed with water and brine, dried (MgSO4), concentrated in vacuo and purified by silica gel chromatography to provide carbonic acid 4-fluoro-2-methyl-5-nitrophenyl ester methyl ester (2.0 g, 11% yield). 1H NMR (300 MHz, DMSO-d6): δ 8.14 (d, J=6.9, 1H), 7.60 (d, J=12.0 Hz, 1H), 3.86 (s, 3H), 2.25 (s, 3H).

Workup

extractionextracted with ethyl acetate (3×100 mL)
washThe extracts were washed with water and brine
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo
custompurified by silica gel chromatography

Sources & evidence

ORD record: ord-3f80605c848141c08fb5d4f87ef71bf0
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08278331B2

Reaction notes

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