Nitric Acid → 6-Fluoro-2-methyl-3-nitrobenzoic acid
Reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1[C:4]([OH:6])=[O:5].[N+:12]([O-])([OH:14])=[O:13]>S(=O)(=O)(O)O>[F:1][C:2]1[C:3]([C:4]([OH:6])=[O:5])=[C:7]([CH3:11])[C:8]([N+:12]([O-:14])=[O:13])=[CH:9][CH:10]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -15 °C
Procedure
2-Fluoro-6-methylbenzoic acid (40 g, 0.26 mol) was dissolved in 320 mL of sulfuric acid and chilled to −15° C. To this was added 14 mL of fuming nitric acid in 60 mL of sulfuric acid over a 10 minute period. Once the addition was complete, the mixture was stirred at 0° C. for 1 hour, then poured into ice water, and stirred. The resulting solids were collected and then dissolved in EtOAc, which was washed with water, dried over sodium sulfate and concentrated to 50 g (97%) of the title compound.