Nitric Acid → 1-Methyl-2-nitro-4-(pentafluoroethyl)benzene

A mixture of concentrated nitric acid (1 ml) and concentrated sulphuric acid (2 ml) was added to a cooled stirred suspension of 4-pentafluoroethyltoluene (2.1 g) in concentrated sulphuric acid (5 ml) whilst maintaining the temperature below 5° C. The mixture was stirred at 0° C. for 10 minutes, allowed to warm to room temperature and stirred for 1.5 hours. It was poured onto ice (30 ml) and extracted with ether (2×25 ml). The combined organic extracts were washed with aqueous sodium carbonate (2M, 2×25 ml), water (25 ml), saturated aqueous sodium chloride solution (25 ml), dried (anhydrous magnesium sulphate) and filtered. The filtrate was evaporated to dryness to give 2-nitro-4-pentafluoroethyltoluene (2.04 g) as a pale yellow oil NMR (CDCl3) 2.7(s,3H), 7.45(d,1H), 7.7(d,1H), 8.1(s,1H).

1. additionwas added to a cooled
2. temperaturewhilst maintaining the temperature below 5° C
3. stirringThe mixture was stirred at 0° C. for 10 minutes
4. stirringstirred for 1.5 hours
5. additionIt was poured onto ice (30 ml)
6. extractionextracted with ether (2×25 ml)
7. washThe combined organic extracts were washed with aqueous sodium carbonate (2M, 2×25 ml), water (25 ml), saturated aqueous sodium chloride solution (25 ml)
8. dry with materialdried (anhydrous magnesium sulphate)
9. filtrationfiltered
10. customThe filtrate was evaporated to dryness

ORD record

ord-b50ac3d0339241db910625a5eca87578

Source dataset

uspto-grants-1999_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05859283