Electric Literature of 19056-40-7, A common heterocyclic compound, 19056-40-7, name is 4-Bromo-3-methoxyaniline, molecular formula is C7H8BrNO, 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.
To a suspension of 4-bromo-3-methoxyaniline (2.5 g, 12.4 mmol) and potassium phosphate, tribasic (1.08 g, 6.19 mmol) in acetonitrile (40 mL) at 0°C, was added 2,4- dibromobutyryl chloride (1.64 mL, 12.4 mmol). The mixture was brought to rt and stirredfor 1 h. Aqueous NaOH (50percent) (5 mL, 12.37 mmol) was added, and the mixture was stirred at rt for 4 h. The reaction mixture was filtered through CELITE®, which was rinsed with acetonitrile. The filtrate was concentrated. The product was purified by flash chromatography (0-50percent EtOAc/Hex gradient) to obtain Intermediate 4 (3.5 g, 66percent yield) as a pinkish colored solid. MS(ESI) m/z: 350.0 (M+H) ?H NMR (300 MHz, chloroform-d) oe ppm 7.77 (d, J=2.27 Hz, 1 H) 7.53 (d, J=8.69 Hz, 1 H) 6.82 (dd, J=8.69, 2.27 Hz, 1 H) 4.61 (dd, J=7.18, 3.40 Hz, 1 H) 4.05 (dt, J=9.73, 7.22 Hz, 1 H) 3.94 (s, 3 H) 3.85 (ddd, J10.01, 7.55, 2.83 Hz, 1 H) 2.69 – 2.83 (m, 1 H) 2.48 (ddt, J=14.35, 6.70, 3.26, 3.26 Hz, 1 H).
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; GLUNZ, Peter W.; SITKOFF, Doree F.; BODAS, Mandar Shrikrishna; YADAV, Navnath Dnyanoba; PATIL, Sharanabasappa; RAO, Prasanna Savanor Maddu; THIYAGARAJAN, Kamalraj; MAISHAL, Tarun Kumar; (498 pag.)WO2016/144936; (2016); A1;,
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