Electric Literature of 791642-68-7,Some common heterocyclic compound, 791642-68-7, name is 4-Bromo-1-iodo-2-methoxybenzene, molecular formula is C7H6BrIO, 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.
(Reference Example 4) 1-(4′-bromo-2′-methoxy-[1,1′-biphenyl]-4-yl)cyclopropanecarboxylic acid ethyl ester A 1,4-dioxane (15 ml)-water (10 ml) solution of 1.2 g (3.8 mmol) of 4-bromo-1-iodo-2-methoxybenzene synthesized in analogy to Reference Example 3, 1.1 g (3.5 mmol) of 1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]cyclopropanecarboxylic acid ethyl ester (synthesized in accordance with the process described in ) and 1.1 g (10 mmol) of sodium carbonate was degassed and was purged with nitrogen. Next, 0.10 g (0.12 mmol) of [1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloride methylene chloride adduct was added. The mixture was stirred in a nitrogen atmosphere for 1.5 hours while performing heating at 80C. After the completion of the reaction, water was added to the reaction mixture liquid, and the mixture was extracted with ethyl acetate. The organic phase was washed with saturated brine, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (eluting solvent: hexane:ethyl acetate = 94:6 to 75:25 (V/V)), and the fraction containing the target compound was concentrated under reduced pressure and was dried by vacuum heating to give the title compound weighing 0.72 g (1.9 mmol, yield 55%) as a white solid. Mass spectrum (EI, m/z): 374 [M]+. 1H-NMR spectrum (400MHz, CDCl3) delta: 7.45-7.41 (2H, m), 7.39-7.35 (2H, m), 7.19 (1H, d, J = 8.0 Hz), 7.15 (1H, dd, J = 8.0, 1.8 Hz), 7.10 (1H, d, J = 1.8 Hz), 4.12 (2H, q, J = 7.1 Hz), 3.81 (3H, s), 1.61 (2H, dd, J = 7.0, 4.0 Hz), 1.22 (2H, dd, J = 7.0, 4.0 Hz), 1.19 (3H, t, J = 7.1 Hz).
The synthetic route of 791642-68-7 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; UBE Industries, Ltd.; IWASE, Noriaki; NISHIDA, Hiroshi; OKUDO, Makoto; ITO, Masaaki; KONO, Shigeyuki; MATOYAMA, Masaaki; USHIYAMA, Shigeru; OKANARI, Eiji; MATSUNAGA, Hirofumi; NISHIKAWA, Kenji; KIMURA, Tomio; (54 pag.)EP3162801; (2017); A1;,
Iodide – Wikipedia,
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