Synthetic Route of 29578-39-0,Some common heterocyclic compound, 29578-39-0, name is 1-Bromo-3-fluoro-5-methoxybenzene, molecular formula is C7H6BrFO, 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 solution of 3-bromo-5-fluoroanisole (250 mg, 1.22 mmol, 1 equiv) in anhydrous THF was added granules of magnesium (32 mg, 1.28 mmol, 1.05 equiv) under nitrogen. The mixture was heated to 60 C for 2 h. After cooling down to room temperature, 6-bromopyridin-2-yl carboxaldehyde (271 mg, 1.47 mmol, 1.2 equiv) was added and the reaction mixture was stirred at 80 C overnight. The reaction was cooled to room temperature, quenched with brine and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated to dryness under vacuum. The product was purified by column chromatography (hexane/ethyl acetate 8:2) to afford the analytically pure compound in 21% yield (80 mg). C13H11BrFNO2; MW 312; 1H NMR (acetone-d6): delta 7.74 (t, J = 7.6 Hz, 1H), 7.64-7.61 (m, 1H), 7.47 (dd, J = 0.9 Hz, J = 7.2 Hz, 1H), 6.92-6.90 (m, 1H), 6.81 (ddd, J = 0.6 Hz, J = 1.3 Hz, J = 9.1 Hz, 1H), 6.59 (dt, J = 2.5 Hz, J = 10.7 Hz, 1H), 5.77 (d, J = 4.7 Hz, 1H), 5.35 (d, J = 4.7 Hz, 1H), 3.79 (s, 3H); 13C NMR (acetone-d6): delta 165.8, 165.3, 140.8, 127.5, 120.3, 109.4, 106.1, 105.9, 101.0, 100.8, 75.8, 56.0; LC/MS m/z: 312-314 (M + H)+.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-3-fluoro-5-methoxybenzene, its application will become more common.
Reference:
Article; Wetzel, Marie; Gargano, Emanuele M.; Hinsberger, Stefan; Marchais-Oberwinkler, Sandrine; Hartmann, Rolf W.; European Journal of Medicinal Chemistry; vol. 47; 1; (2012); p. 1 – 17;,
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