Electric Literature of 262587-05-3, These common heterocyclic compound, 262587-05-3, name is 1-Bromo-3-(difluoromethoxy)benzene, 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.
93 mg of 1 -bromo-3(dofluoromethoxy)benzene (0.42 mmol; 1.00 eq) and the successively 142 mg of 1 -[3-methyl-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)phenyl]azetidine-3-carboxylic acid (preparation 9; 0.42 mmol; 1.00 eq) dissolved in 4 mE of DME, 3.4 mg of Pd(dppf)C12, CH2C12 (0.01 eq.) and finally 127 mg of CsF (0.83 nnol; 2.00 eq) were introduced into a microwave- resistant 10 mE reaction vessel. The reaction mixture was microwave-irradiated for 1 h at 120 C. The reaction medium was then taken up with ethyl acetate and water, while adjusting the pH to 6, and then extracted with ethyl acetate and washed with brine. The organic phase was dried over magnesium suflate, filtered and concentrated under vacuum. The residue was purified by flash chromatography (l3iotage 10 g silica 15-40 jtmlliquid deposit in dichloromethane) using a cyclohexane/0% to 100% dichloromethane gradient. The fractions containing the targeted product were combined and then evaporated, under reduced, pressure to give 99 mg of title compound in the form of a colorless oil,Yld: 33%.10548] ?H NMR (300 MHz, CHC13-d) oeppm 2.24 (s, 3H)3.41-3.49 (m, 1H) 3.62 (s, 3H) 3.92-4.02 (m, 4H) 6.18 (s, 1H) 6.32 (s, 1H) 6.43 (t, J=74 Hz, 1H) 6.68 (s, 1H) 6.93-6.96 (m, 1H) 7.19-7.3 1 (m, 3H).EC-MS mlz (M+H): 348.
The synthetic route of 262587-05-3 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; INVENTIVA; BOUBIA, Benaissa; MASSARDIER, Christine; GUILLIER, Fabrice; POUPARDIN, Olivia; TALLANDIER, Mireille; AMAUDRUT, Jerome; BONDOUX, Michel; FEENSTRA, Roelof Williem; VAN DONGEN, Maria Johana Petronella; (207 pag.)US2017/66717; (2017); A1;,
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