Synthesis
General method: o-tolyl acetate (3.18 g, 15 mmol) and N-bromosuccinimide (2.67 g, 15 mmol) were dissolved in dry carbon tetrachloride (60 ml), and the reaction mixture was stirred for 1 hr under the irradiation of 150 W tungsten lamp. After completion of the reaction, the mixture was cooled to room temperature and the precipitated succinimide was removed by filtration. The filtrate was concentrated under reduced pressure to remove the solvent and the resulting crude product was purified by silica gel column chromatography using a solvent mixture of ethyl acetate with petroleum ether (60-80 °C boiling range, 10% v/v) as eluent to give phenyl 2-(bromomethyl)acetate (3a). It was further recrystallized from a mixed solvent of ethyl ether and petroleum ether (60-80 °C boiling range) to obtain colorless shiny granular crystals.
References
[1] Organic Letters, 2009, vol. 11, # 16, p. 3670 - 3673
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1993, # 12, p. 1359 - 1366
[3] Tetrahedron Letters, 2011, vol. 52, # 18, p. 2423 - 2423
[4] Inorganic Chemistry, 2017, vol. 56, # 1, p. 470 - 479
[5] Acta Chemica Scandinavica, 1997, vol. 51, # 12, p. 1162 - 1168
