These common heterocyclic compound, 36282-26-5, name is 2-Bromo-4-fluorobenzonitrile, 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. name: 2-Bromo-4-fluorobenzonitrile
To a stirred solution of 2-bromo-4-fluorobenzonitrile (5 g, 25 mmol) in ether (100 mL) was added MeMgBr (25 mL, 75 mmol) at room temperature. The solution was stirred at room temperature for 0.5 hour before Ti(Oi-Pr)4 (41 mL, 25 mmol) was added and the resulting mixture was heated to reflux for 6 hours. Aqueous NaOH (10%, 200 mL) solution was then slowly added to the reaction mixture at 0 C and the reaction mixture was stirred at room temperature for additional 30 minutes. After dilution with aq. Na2C03 (5%, 400 mL) solution, it was extracted with t-BuOMe (100 mL x 3). The combined organic layers were concentrated under reduced pressure. The residue obtained was diluted with aq. HC1 solution (5%) and the aqueous layer was washed with t-BuOMe (50 mL x 2) and basified with 20% aq. NaOH to pH~ 10. The resulting aqueous layer was further extracted with t-BuOMe (100 mL x 3). The combined organic layers were then dried over anhy. Na2S04, filtered, and concentrated in vacuo to give a crude product, which was purified by column chromatography to give the title product (3.0 g, yield 51.7%) as yellowish oil. MS: 231.7 (M+H+, IBr)
The synthetic route of 2-Bromo-4-fluorobenzonitrile has been constantly updated, and we look forward to future research findings.
Reference:
Patent; F. HOFFMANN-LA ROCHE AG; AEBI, Johannes; AMREIN, Kurt; CHEN, Wenming; HORNSPERGER, Benoit; KUHN, Bernd; LIU, Yongfu; MAERKI, Hans P.; MAYWEG, Alexander V.; MOHR, Peter; TAN, Xuefei; WANG, Zhanguo; ZHOU, Mingwei; WO2013/79452; (2013); A1;,
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