Some common heterocyclic compound, 5279-32-3, name is 5,6-Dibromobenzo[d][1,3]dioxole, molecular formula is C7H4Br2O2, 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. Safety of 5,6-Dibromobenzo[d][1,3]dioxole
Under nitrogen atmosphere, 5,6-Dibromo-1,3-benzodioxole (13a, 1.58 g, 5.64 mmol), zinc(II)cyanide (670 mg, 5.71 mmol) and [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (208 mg, 284 mumol) were dissolved in anhydrous dimethylacetamide (12 mL) andstirred for 3 h at 150 C. Subsequently, the mixture was diluted with ethyl acetate (50 mL),washed with water (2 × 50 mL), the organic layer dried over magnesium sulfate and the solventremoved in vacuo. The crude product was purified by column chromatography using silica anddichloromethane as eluent (Rf = 0.50) to obtain a colourless solid (829 mg, 4.82 mmol, 85%).1H NMR (500MHz, CDCl3, 300 K): delta = 7.14 (s, 2H), 6.21 (s, 2H) ppm;13C NMR (125 MHz, CDCl3, 300 K): delta = 151.7 (2C), 115.5 (2C), 112.8 (2C), 111.0 (2C), 104.0 ppm;MS (EI, 70 eV): m/z (%) = 172 (100) [M]+;HR-MS (EI, 70 eV): m/z = calcd. for C9H4N2O2 [M]+ 172.0267, found 172.0273.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5279-32-3, its application will become more common.
Reference:
Article; Hamer, Sebastian; Roehricht, Fynn; Jakoby, Marius; Howard, Ian A.; Zhang, Xianghui; Naether, Christian; Herges, Rainer; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 1331 – 1338;,
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