Nitric Acid → Methyl 5-chloro-2-ethyl-3-nitrobenzoate

Temperature

-5 °C

A solution of methyl 5-chloro-2-ethylbenzoate (1.08 g, 5.4 mmol) in concentrated sulphuric acid (7.0 ml) was cooled to −5° C. in an acetone/ice bath. A mixture of 70% nitric acid (0.45 ml, 7.1 mmol) and concentrated sulphuric acid (0.5 ml) was added dropwise to the reaction mixture at −5° C. over 15 minutes. The resulting pale yellow reaction mixture was stirred at −5° C. for 1 hour before being poured onto ice (100 ml) and extracted with CH2Cl2 (3×20 ml). The combined organic phases were washed with deionized water (20 ml), brine (20 ml), dried over Na2SO4, filtered and concentrated in-vacuo. The resulting oil was added to a solution containing methanol (25 ml) and thionyl chloride (0.75 ml) at 0° C. Following addition, the mixture was heated under gentle reflux for 6 hours, before cooling to room temperature and concentrating in-vacuo to give the title compound (1.2 g) as an orange oil which was used without further purification in the next step.

1. additionwas added dropwise to the reaction mixture at −5° C. over 15 minutes
2. additionbefore being poured onto ice (100 ml)
3. extractionextracted with CH2Cl2 (3×20 ml)
4. washThe combined organic phases were washed with deionized water (20 ml), brine (20 ml)
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated in-vacuo
8. additionThe resulting oil was added to a solution
9. additioncontaining methanol (25 ml) and thionyl chloride (0.75 ml) at 0° C
10. additionaddition
11. temperaturethe mixture was heated
12. temperatureunder gentle reflux for 6 hours
13. temperaturebefore cooling to room temperature
14. concentrationconcentrating in-vacuo

ORD record

ord-248c89ca6d784f4a812ab4fda9978647

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09376422B2