These common heterocyclic compound, 116632-39-4, name is 5-Bromo-2-iodotoluene, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Recommanded Product: 116632-39-4
To a solution of 4-bromo-1-iodo-2-methylbenzene (0.24 mL, 1.6 mmol) in tetrahydrofuran (5 mL) at -78 C. was added n-butyl lithium (2.5 M in hexane, 0.8 mL, 2.0 mmol) dropwise over 15 minutes. The reaction mixture was stirred at -78 C. for 30 minutes, treated with neat cyclobutanone (0.12 mL, 1.6 mmol) dropwise over 10 minutes and stirred at -78 C. for an additional 1.5 hours. The reaction was quenched with saturated aqueous ammonium chloride solution, warmed to room temperature and extracted with ethyl acetate (2*). The combined organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo to afford 500 mg yellow semi-solid, which was purified by flash chromatography (12 g silica, 0-50% ethyl acetate/heptane, 18 column volumes). Product fractions were combined and concentrated in vacuo to afford the title compound as a colorless waxy solid (290 mg, 73% yield). GCMS 240/242 (M)+; 1H NMR (400 MHz, CDCl3) delta 7.23-7.31 (m, 2H), 7.11 (d, J=8.20 Hz, 1H), 2.55-2.64 (m, 2H), 2.28-2.38 (m, 5H), 2.07-2.20 (m, 1H), 1.93 (s, 1H), 1.62-1.74 (m, 1H).
The synthetic route of 5-Bromo-2-iodotoluene has been constantly updated, and we look forward to future research findings.
Reference:
Patent; PFIZER INC.; Bhattacharya, Samit; Cameron, Kimberly; Dowling, Matthew; Fernando, Dilinie; Ebner, David; Filipski, Kevin; Kung, Daniel; Lee, Esther; Smith, Aaron; Tu, Meihua; US2013/267493; (2013); A1;,
Iodide – Wikipedia,
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