Electric Literature of 19752-55-7,Some common heterocyclic compound, 19752-55-7, name is 1-Bromo-3,5-dichlorobenzene, molecular formula is C6H3BrCl2, 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 3,5-dichlorobromobenzene (225 mg, 1 mmol), 4-hydroxypiperidine (101 mg, 1 mmol), BINAP (31.2 mg, 0.05 mmol), and NaOtBu (114 mg, 1.2 mmol) in toluene (3 mL) under argon, was added Pd(OAc)2 (8 mg, 0.03 mmol). The resulting reaction mixture was stirred at 100oC for 4 h. The flask was cooled to room temperature and then partitioned between ethyl acetate (20 mL) and water (20 mL). The organic layer was separated, washed with brine, and dried over Na2SO4. After evaporation of the volatiles, the residue was subjected to column chromatography, eluting with hexane/ethyl acetate (4/1) to afford 1-(3,5-dichlorophenyl)piperidin-4-ol as a colorless oil (210 mg, 85percent) as well as a small amount of 1-(3,5-dichlorophenyl)piperidin-4-one (10 mg, 5percent). A mixture of the above product (210 mg, 0.85 mmol) and Dess-Martin periodinane (424 mg, 1 mmol) were dissolved in DCM (4 mL) and stirred for 1 h at room temperature. After evaporation of the volatiles, the residue was subjected to column chromatography, eluting with hexane/ethyl acetate (15/1) to afford 1 as a colorless oil (169 mg, 77percent). 1H NMR (500 MHz, CDCl3) delta 6.82 (d, J = 2.0 Hz, 1H), 6.78 (d, J = 1.5 Hz, 2H), 3.61 (t, J = 6.0Hz, 4H), 2.55 (t, J = 6.0 Hz, 4H); 13C NMR (125 MHz, CDCl3) delta 207.3, 150.7, 136.0X2, 119.1, 113.5X2, 47.7, 40.5; MS (ESI): m/z 244.0 [M+H]+.
The synthetic route of 19752-55-7 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Zhang, Yinan; Silverman, Richard B.; Tetrahedron Letters; vol. 54; 6; (2013); p. 573 – 575;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics