Synthesis
General procedure for the synthesis of methyl 4-(2-bromoacetyl)benzoate from methyl 4-acetylbenzoate: Bromine (2.71 mL, 52.5 mmol) was added dropwise to a solution of methyl 4-acetylbenzoate (8.91 g, 50.0 mmol) in acetic acid (80 mL). The reaction mixture was stirred at room temperature for 2 hours. Upon completion of the reaction, the mixture was cooled to 0 °C and filtered to collect the solid. The resulting precipitate was washed with a 1:1 mixed methanol-water solution and subsequently dried to afford methyl 4-(2-bromoacetyl)benzoate (10.6 g, 82% yield) as a brown solid. The product was characterized by 1H NMR (400 MHz, CDCl3) with chemical shifts of δ 8.19-8.12 (m, 2H), 8.04 (d, J = 8.5 Hz, 2H), 4.47 (s, 2H), 3.96 (s, 3H).
References
[1] Journal of the American Chemical Society, 2000, vol. 122, # 39, p. 9361 - 9366
[2] Patent: WO2006/78698, 2006, A1. Location in patent: Page/Page column 64
[3] Patent: US2012/196869, 2012, A1. Location in patent: Paragraph 0467; 0468; 0469
[4] Inorganic Chemistry, 2018, vol. 57, # 1, p. 120 - 128
[5] Patent: WO2008/33745, 2008, A2. Location in patent: Page/Page column 70-71
