Related Products of 2635-13-4,Some common heterocyclic compound, 2635-13-4, name is 5-Bromobenzo[d][1,3]dioxole, molecular formula is C7H5BrO2, 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 vigorously stirred solution of 5-bromobenzo[d][1,3]dioxole(1 equiv, 8 g, 4.82 mL, 39.8 mmol) and silver trifluoroacetate (1.1 equiv, 9.67 g, 43.8 mmol) in DCM (100 mL) at 20 C was added dropwise over 1 h a solution of iodine (1.1 equiv, 11.1 g, 43.8 mmol) in a mixture of DCM (200 mL) and diethylether (100 mL). The mixture was then allowed back to room temperature and stirred overnight. The reaction mixture was quenched with a 10% (w/w) solution of sodium thiosulfate, the phases were separated and the aqueous phase was extracted with diethylether. The combined organic phases were washed with a saturated NaHCO3 solution, brine, and dried over sodium sulfate. The solvent was removed under reduced pressure and the crude product was recrystallized from methanol yielding 6-bromo-5-iodobenzo[d][1,3]dioxole (11.1 g,33.9 mmol, 85%). 1H NMR (CDCl3, 400 MHz): 7.24 (s, 1H), 7.08 (s, 1H), 5.99 (s, 2H)ppm. 13C NMR (CDCl3, 101 MHz): d149.1, 147.9, 120.7, 119.1, 112.7,102.3, 89.3 ppm.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromobenzo[d][1,3]dioxole, its application will become more common.
Reference:
Article; Dherbassy, Quentin; Wencel-Delord, Joanna; Colobert, Francoise; Tetrahedron; vol. 72; 34; (2016); p. 5238 – 5245;,
Bromide – Wikipedia,
bromide – Wiktionary