Nitric Acid → 5-Bromo-2-methyl-3-nitrobenzoic acid

Temperature

-2.5 °C

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 to 0° C. over 15 minutes. The yellow reaction mixture was stirred at −5 to 0° 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. LC-MS 57%, 1.82 min (3.5 minute LC-MS method), no ionization; 1H NMR (500 MHz, DMSO-d6) δ ppm 8.29 (s, 1H) 8.13 (d, J=1.58 Hz, 1H) 2.43 (s, 3H).

1. additionwas added dropwise to the reaction mixture at −5 to 0° C. over 15 minutes
2. customformed
3. additionThe reaction mixture was poured onto ice (150 g)
4. filtrationthe precipitate was then collected by filtration
5. customdried

ORD record

ord-4f8331b6a3544962802910b40dd0645a

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08765732B2