Reference of 5905-69-1, A common heterocyclic compound, 5905-69-1, name is 1-Bromo-4-(difluoromethoxy)benzene, molecular formula is C7H5BrF2O, 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 stirred solution of bromophenol derivative AM (2.0 g, 8.97 mmol) in 1,4-dioxane (40 mL) were added bis(pinacolato)diboron (2.28 g, 8.97 mmol) and KOAc (2.64 g, 26.90 mmol) at RT under inert atmosphere, and the mixture was degassed for 20 min by purging with argon. To this solution, Pd(dppf)2Cl2 (0.33 g, 0.45 mmol) was added, and the mixture was degassed for a further 10 min. The reaction mixture was then heated to 80 C. and stirred for 3 h at this temperature. Progress of the reaction was monitored by TLC. The reaction mixture was then cooled to RT and diluted with EtOAc (30 mL). The resultant solution was filtered through a Celite pad, and the filtrate was then concentrated in vacuo. The crude compound was purified by silica gel column chromatography (eluting with 5-10% EtOAc gradient in hexanes) to afford AN (1.72 g, 6.37 mmol, 71%). 1H NMR (500 MHz, CDCl3): delta 7.81 (d, J=8.5 Hz, 2H), 7.09 (d, J=8.5 Hz, 2H), 6.54 (t, JF-H=74.0 Hz, 1H), 1.34 (s, 12H).
The synthetic route of 5905-69-1 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; VIAMET PHARMACEUTICALS, INC.; US2012/329802; (2012); A1;,
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