Some common heterocyclic compound, 3401-47-6, name is 1-Bromo-2-methoxynaphthalene, molecular formula is C11H9BrO, 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. SDS of cas: 3401-47-6
Under argon, in a flame-dried vessel, a solution of 1-bromo-2-methoxynaphthalene (7.67 g, 32.36) in THF (50 ml) was added dropwise to the magnesium (0.905 g, 37.2 mmol) in THF (15 ml). The reaction mixture was stirred at room temperature for 2 h then at 50C for 1h. It was then cooled to -78C and trimethylborate (11.4 ml, 101.7 mmol) was slowly added. After 2 h at -78C, the mixture was allowed to warm to room temperature and stirred overnight. After addition of water (40 ml), THF was removed under reduced pressure. The mixture was extracted with dichloromethane; the combined organic phases were dried over MgSO4, filtered and concentrated. Recrystallization from dichloromethane gave the boronic acid as a white powder (80% yield). 1H NMR (400.14 MHz, CDCl3): d = 4.08 (s, 3H), 6.22 (s, 2 H), 7.28 (d, J = 9.1 Hz, 1H), 7.34-7.43 (m, 1H), 7.47-7.56 (m, 1H), 7.80 (d, J = 8.1 Hz, 1H), 7.98 (d, J = 8.9 Hz, 1H), 8.86 ppm (d, J = 9.1 Hz, 1H); 13C{1H} NMR (75.47 MHz, [D6]DMSO): d = 56.1, 113.7, 121.8, 122.7, 125.8, 127.4, 127.8, 128.5, 129.4, 135.6, 159.0
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3401-47-6, its application will become more common.
Reference:
Article; Castillo, Angelica Balanta; Perandones, Bernabe F.; Zangrando, Ennio; Gladiali, Serafino; Godard, Cyril; Claver, Carmen; Journal of Organometallic Chemistry; vol. 743; (2013); p. 31 – 36;,
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