Electric Literature of 81474-46-6, These common heterocyclic compound, 81474-46-6, name is Methyl 4-bromo-7-methoxybenzo[d][1,3]dioxole-5-carboxylate, 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 solution of 8 (14.4 g, 50.0 mmol) in THF (100.0 mL) at 0 C was added dropwise DIBALH (1.0 mol/L in hexane, 150.0 mL, 150.0 mmol). This mixture was stirred at 0 C for 30 min, then quenched by aq Rochelle salt (1 mol/L, 200 mL). It was evaporated in vacuo to remove the organic solvents, and water (100 mL) and CH2Cl2 (100 mL) was added to the residue. The organic layer was separated, and the water layer was extracted with CH2Cl2 (100 mL×2). The combined organic layer was washed with brine (150 mL×2), dried over anhydrous Na2SO4, filtered through a short silica gel pad and concentrated in vacuo to give 9 (13.0 g) as a white solid. Yield: 99%; mp 139-141 C; 1H NMR (300 MHz, CDCl3): delta 6.71 (s, 1H), 6.06 (s, 2H), 4.68 (d, 2H, J=6.24 Hz), 3.91 (s, 3H), 1.88 (t, 1H, J=6.24 Hz); 13C NMR (75 MHz, CDCl3): delta 147.0, 142.9, 135.0, 133.5, 108.4, 102.0, 93.3, 64.5, 56.7; IR (KBr) 3213, 2904, 1628, 1446, 1342, 1161, 1106, 1036, 699 cm-1; HRMS (ESI): calcd for C9H9BrO4Na [M+Na]+ 282.9576, found 282.9571.
The synthetic route of 81474-46-6 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Ni, Jizhi; Xiao, Heping; Weng, Lipeng; Wei, Xiaofeng; Xu, Youjun; Tetrahedron; vol. 67; 29; (2011); p. 5162 – 5167;,
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