Uses
2,6-Difluoro-3-nitrotoluene used as a intermediate in organic synthesis, pharmaceutical and chemical research.
Synthesis
Example A36: 65% HNO3 (11.4 g, 0.12 mol) was slowly added dropwise to a solution of 1,3-difluoro-2-methylbenzene (15 g, 0.12 mol) dissolved in H2SO4 (100 mL) at -10°C. The reaction mixture was stirred continuously at this temperature for 30 minutes. Upon completion of the reaction, the mixture was carefully poured into ice water and subsequently extracted with EtOAc (3 x 200 mL). The combined organic phases were washed with saturated brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford the target product 1,3-difluoro-2-methyl-4-nitrobenzene (16 g, 78% yield). The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3): δ 7.80 (m, 1H), 6.8-7.1 (m, 1H), 2.30 (s, 3H).
References
[1] Chemical and Pharmaceutical Bulletin, 1982, vol. 30, # 10, p. 3530 - 3543
[2] Patent: US2008/90856, 2008, A1. Location in patent: Page/Page column 40
[3] Patent: WO2010/51373, 2010, A1. Location in patent: Page/Page column 64
[4] Patent: WO2013/36232, 2013, A2. Location in patent: Paragraph 00273
[5] Patent: US2014/315917, 2014, A1. Location in patent: Paragraph 0506
