Nitric Acid → HCID 70873959, compound

Temperature

0 °C

A solution of methyl 2-bromo-5-chlorobenzoate (10 g, 40 mmol) in concentrated H2SO4 (48 ml, 910 mmol) was cooled to −5° C. in an acetone/ice bath in air. A mixture of concentrated nitric acid (3.35 ml, 52 mmol) and concentrated H2SO4 (3.4 ml, 64 mmol) was added dropwise to the reaction mixture at 0° C. over 30 minutes. The yellow reaction mixture was stirred at 0° C. for 1.5 hours before being poured onto ice. EtOAc (150 ml) was added and the phases were separated. The organic phase was washed with deionized water (3×50 ml) followed by brine (50 ml). The organic phase was dried over MgSO4, filtered and concentrated under reduced pressure to give 12.0 g (60%) of the title compound material as a pale yellow oil which solidified upon standing. This material contained 40% of the 6-nitro isomer. This material was used without further purification. LC-MS 91%, m/z=no ionisation, 1H NMR (500 MHz, Chloroform-d) δ 7.86 (1H, d, J=2.52 Hz), 7.77 (1H, d, J=2.52 Hz), 3.99 (3H, s).

1. additionwas added dropwise to the reaction mixture at 0° C. over 30 minutes
2. additionbefore being poured onto ice
3. customthe phases were separated
4. washThe organic phase was washed with deionized water (3×50 ml)
5. dry with materialThe organic phase was dried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure

ORD record

ord-85153c899ea04262a60496d443ab92ab

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09376422B2