Synthesis
The general procedure for the synthesis of 2-(bromomethyl)-1-methyl-3-nitrobenzene from (2-methyl-6-nitrophenyl)methanol was as follows: benzyl alcohol (2.52 g, 15.07 mmol) was dissolved in CH2Cl2 (0.12 M) under argon protection, and cooled to -78°C. A 1.0 M CH2Cl2 solution of BBr3 was added slowly and dropwise (23 mL 22.6 mmol). The reaction mixture was stirred overnight at room temperature and then diluted with H2O (150 mL). The organic layer was separated, washed with brine, dried over MgSO4 and concentrated to give 2.97 g (86% yield) of 2-methyl-6-nitrobenzyl bromide as a brown solid.1H NMR (400 MHz, CDCl3) δ 2.53 (s, 3H), 4.72 (s, 2H), 7.36 (t, J = 7.8 Hz, 1H), 7.46 (d, J = 7.6 Hz, 1H), 7.75 (d, J = 8.1 Hz, 1H).
References
[1] Journal of Chemical Research, Miniprint, 2001, # 10, p. 1023 - 1055
[2] Patent: WO2006/128142, 2006, A2. Location in patent: Page/Page column 30
[3] Journal of Organic Chemistry, 2011, vol. 76, # 9, p. 3484 - 3497
[4] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 20, p. 6574 - 6595
[5] Patent: WO2013/162072, 2013, A1. Location in patent: Page/Page column 950; 951
