As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 891785-18-5, name is 3-(Benzyloxy)-5-bromo-2-chloropyridine, molecular formula is C12H9BrClNO, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. Computed Properties of C12H9BrClNO
To a suspension of 68 3-(benzyloxy)-5-bromo-2-chloropyridine (25.7 mg, 86.0 mmol) and 41 potassium phosphate (54.9 g, 259 mmol) in 9 tetrahydrofuran (180 mL) were added successively 14 water (130 mL), 17 (E)-2-(3-methoxyprop-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (20.1 mL, 95.0 mmol) and [1,1?-bis(diphenylphosphino)-ferrocene]palladium(II) dichloride dichloromethane adduct (3.54 g, 4.33 mmol), and the mixture was stirred at room temperature for 2 hr. [1,1?-Bis(diphenylphosphino)-ferrocene]palladium(II) dichloride dichloromethane adduct (1.70 g, 2.04 mmol) was added again thereto, and the mixture was stirred at room temperature for 3 hr, warmed to 33 C., and stirred for 1 hr. The reaction solution was diluted with ethyl acetate (180 mL), and the insoluble substance was removed by filtration. The organic layer of the filtrate was washed with water and saturated brine, silica gel (50 g) was added thereto, and the mixture was stirred at room temperature for 1 hr. The silica gel was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate=15:1 to 4:3) to give 70 (E)-3-(benzyloxy)-2-chloro-5-(3-methoxyprop-1-en-1-yl)pyridine (20.9 g, yield 83%). 1H-NMR (DMSO-D6) delta: 3.29 (3H, s), 4.06-4.07 (2H, m), 5.29 (2H, s), 6.59-6.60 (2H, m), 7.32-7.49 (5H, m), 7.81 (1H, d, J=1.8 Hz), 8.02 (1H, d, J=2.1 Hz).
With the rapid development of chemical substances, we look forward to future research findings about 891785-18-5.
Reference:
Patent; JAPAN TOBACCO INC.; NAGAMORI, Hironobu; NISHIMARU, Tatsuya; TAKAGI, Masaki; MITANI, Ikuo; NAKAGAWA, Yuichi; US2019/152926; (2019); A1;,
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