Synthesis
General procedure for the synthesis of 2-iodobenzyl bromide from 2-iodobenzyl alcohol: 48% hydrobromic acid (10 mL) and 98% sulfuric acid (2 mL) were added to 2-iodobenzyl alcohol (0.94 g, 4.0 mmol). The resulting suspension was placed in an oil bath and heated and stirred at 150 °C for 2 hours. After completion of the reaction, the mixture was cooled to room temperature and extracted with dichloromethane (2 x 10 mL). The organic layers were combined, dried with anhydrous magnesium sulfate and concentrated under reduced pressure to give the crude product. The crude product was purified by fast column chromatography (silica gel, 0-20% dichloromethane/hexane gradient elution) to afford the target compound 2-iodobenzyl bromide (1.0 g, 84% yield).
References
[1] Tetrahedron, 2005, vol. 61, # 13, p. 3311 - 3324
[2] Journal of Organic Chemistry, 2012, vol. 77, # 13, p. 5705 - 5713
[3] Helvetica Chimica Acta, 1995, vol. 78, p. 765 - 771
[4] Tetrahedron, 1993, vol. 49, # 20, p. 4439 - 4446
[5] Tetrahedron, 2002, vol. 58, # 44, p. 9007 - 9018
