Nitric Acid → 5-Bromo-2-methyl-3-nitrobenzoic acid
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].OS(O)(=O)=O.[N+:17]([O-])([OH:19])=[O:18]>>[Br:1][C:2]1[CH:3]=[C:4]([N+:17]([O-:19])=[O:18])[C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]Participants
4
Conditions
- Temperature
- -5 °C
Procedure
A solution of 5-bromo-2-methylbenzoic acid (5.0 g, 23 mmol) in concentrated H2SO4 (27 ml, 512 mmol) was cooled to 5° C. in an acetone/ice bath. A mixture of concentrated nitric acid (1.9 ml, 30 mmol) and concentrated H2SO4 (2.8 ml, 52 mmol) was added dropwise to the reaction mixture at −5 t0° C. over 15 minutes. The yellow reaction mixture was stirred at −5° C. for 2 hours during which time a yellow precipitate formed. The reaction mixture was poured onto ice (150 g) and the precipitate was then collected by filtration. The precipitate was air dried to give the title compound (5.5 g, 52%) as a pale yellow solid.; 1HNMR (500 MHz, DMSO-d6) δ ppm 8.29 (s, 1H) 8.13 (d, J=1.58 Hz, 1H) 2.43 (s, 3H).
Workup
- additionwas added dropwise to the reaction mixture at −5 t0° C
- customformed
- additionThe reaction mixture was poured onto ice (150 g)
- filtrationthe precipitate was then collected by filtration
- customdried
Sources & evidence
- ORD record
- ord-d4165fe27c5a43828b4a051f6686db21
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09376422B2
Reaction notes
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