Nitric Acid → 6-Fluoro-2-methyl-3-nitrobenzoic acid

HRID 1639773Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of nitric acid (6.96 mL, 156 mmol) in sulfuric acid (44 mL) was added a solution of 2-fluoro-6-methylbenzoic acid (16 g, 104 mmol) in concentrated sulfuric acid (150 mL) at −15° C., and the mixture was stirred at 0° C. for 30 min. The reaction solution was poured into ice water (500 mL), and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure to give the title compound as a crudely purified product (20.7 g, yield 100%).

Workup

extractionthe mixture was extracted with ethyl acetate
dry with materialThe extract was dried over anhydrous sodium sulfate
customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-b4d4abd7a25c4389b66f08fafd1999b2
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08110585B2

Reaction notes

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