Synthesis
Preparation of 2-bromo-1-(4-ethylphenyl)ethanone (Chem. Plextr. Reg. No. 2632-14-6): 4'-Ethylacetophenone (9 mL, 60 mmol) was dissolved in 100 mL of anhydrous tetrahydrofuran, and cooled to 0 °C. Subsequently, phenyltrimethylammonium tribromide (22.6 g, 60 mmol) was added in batches and slow formation of precipitate was observed. The reaction mixture was stirred continuously at 0 °C for 1 h, after which stirring was continued at room temperature for 20 min. The concentrated reaction mixture was diluted with 200 mL of ether, washed sequentially with water (3 x 150 mL) and brine, then dried with magnesium sulfate and filtered. The filtrate was concentrated to afford the target product 2-bromo-1-(4-ethylphenyl)ethanone (15.9 g, quantitative yield). Mass spectrometry analysis showed m/z: 227, 229.03 (Br isotope mode); HPLC analysis with a retention time of 18.6 min (purity >99%).
References
[1] Patent: WO2008/84300, 2008, A1. Location in patent: Page/Page column 35
[2] Heterocycles, 1992, vol. 34, # 4, p. 747 - 756
[3] Journal of Heterocyclic Chemistry, 2013, vol. 50, # SUPPL.1, p. E126-E130
[4] Synthetic Communications, 2013, vol. 43, # 19, p. 2603 - 2614
[5] RSC Advances, 2016, vol. 6, # 79, p. 75651 - 75663