Reference of 7025-06-1, These common heterocyclic compound, 7025-06-1, name is 1-Bromo-2-phenoxybenzene, 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.
37A. (1-(2-Phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)methyl 4-methylbenzenesulfonate To a -78° C. solution of 1-bromo-2-phenoxybenzene (283 mg, 1.136 mmol) in anhydrous THF (5 mL) was added dropwise n-BuLi (545 muL of a 2.5 M solution in hexane, 1.363 mmol). The reaction was stirred at -78° C. for 0.5 h, after which a solution of 4-oxocyclohexane-1,1-diyl)bis(methylene)bis(4-methylbenzenesulfonate (1E; 530 mg, 1.14 mmol) in THF (4 mL) was added dropwise. The reaction mixture was slowly warmed to rt and stirred at rt for 2 h. Analytical HPLC showed the reaction was complete. Powdered NaOH (91 mg, 2.27 mmol) was added and the mixture was stirred under reflux for 18 h. The reaction was cooled to rt, diluted with water and extracted with EtOAc (2*). The organic layer was dried (MgSO4) and concentrated in vacuo. The crude oil purified by flash chromatography (SiO2) using a gradient from 0percent to 40percent EtOAc/hexane (15 min) to give the title compound (230 mg, 0.495 mmol, 44percent yield) as a white solid. LCMS [M+H]+=465.1; 1H NMR (CDCl3) delta: 7.85-7.77 (m, 2H), 7.76-7.69 (dd, J=7.9, 1.9 Hz, 1H), 7.41-7.30 (m, 4H), 7.20-7.14 (td, J=7.6, 1.9 Hz, 1H), 7.14-7.06 (m, 2H), 6.98-6.92 (dd, J=7.6, 1.5 Hz, 2H), 6.83-6.76 (dd, J=8.1, 1.4 Hz, 1H), 3.87 (s, 2H), 3.75 (s, 2H), 2.59-2.50 (ddd, J=13.5, 11.3, 4.1 Hz, 2H), 2.48 (s, 3H), 1.98-1.87 (m, 2H), 1.75-1.64 (td, J=11.3, 10.8, 2.7 Hz, 2H), 1.60-1.51 (m, 2H).
The synthetic route of 7025-06-1 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Zhang, Hao; Cheng, Peter T.W.; Chen, Sean; Tao, Shiwei; Wu, Shung C.; Negash, Lidet A.; US2014/275173; (2014); A1;,
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