Synthesis
3,4-Dimethylbenzyl alcohol (1.00 g, 7.34 mmol) was dissolved in dichloromethane (10 mL) at 0 °C and tribromophosphine (1.2 g, 4.41 mmol) was added slowly, keeping the reaction mixture stirred for 3 h at this temperature. Upon completion of the reaction, the reaction was quenched with deionized water (20 mL) followed by extraction with dichloromethane (20 mL x 3). The organic phases were combined, washed with saturated saline (40 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford 3,4-dimethylbenzyl bromide as a colorless oil (1.2 g, yield: 82%). The product was characterized by 1H NMR (400 MHz, CDCl3) with chemical shifts of δ 7.17 (s, 1H), 7.15-7.09 (m, 2H), 4.47 (s, 2H), 2.25 (s, 6H) ppm.
References
[1] Organic and biomolecular chemistry, 2003, vol. 1, # 17, p. 3033 - 3037
[2] Polish Journal of Chemistry, 2007, vol. 81, # 5-6, p. 947 - 969
[3] Patent: WO2013/81642, 2013, A1. Location in patent: Page/Page column 94
[4] Chemical & Pharmaceutical Bulletin, 1983, vol. 31, # 11, p. 4189 - 4192
[5] Pest Management Science, 2000, vol. 56, # 10, p. 875 - 881
