Synthesis
Sodium metal (5.82 g, 0.25 mol) was added to ethanol (240 mL) and stirred until the sodium was completely dissolved. 1-Bromo-4-bromomethylbenzene (37.35 g, 0.15 mol) and diethyl malonate (78 g, 0.49 mol) were then added. The reaction mixture was slowly heated to reflux overnight. After completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was dissolved in distilled water and extracted with ether. The organic layer was washed sequentially with 0.5 N aqueous hydrochloric acid and saturated brine, dried over anhydrous sodium sulfate and concentrated to give diethyl 2-(4-bromobenzyl)malonate (40 g, 85% yield).
References
[1] Patent: WO2010/105179, 2010, A2. Location in patent: Page/Page column 76
[2] Journal of Organic Chemistry, 1984, vol. 49, # 22, p. 4226 - 4237
[3] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1994, vol. 30, # 8, p. 905 - 915
[4] Khimiya Geterotsiklicheskikh Soedinenii, 1993, # 8, p. 1052 - 1062
[5] Tetrahedron Asymmetry, 2001, vol. 12, # 4, p. 585 - 596
