Synthesis method of 3-amino-4-phenylboronic acid pinacol ester
A technology for chlorophenylboronic acid and pinacol ester, which is applied in the field of synthesis of 3-amino-4-chlorophenylboronic acid pinacol ester, can solve the problems of low yield and many steps, and achieves cheap raw materials and purification. Simple, productivity-enhancing effects
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Embodiment 1
[0010] step 1:
[0011] Add 5-bromo-2-chloronitrobenzene (11.8 g, 50.0 mmol), double pinacol borate (12.7 g, 50.0 mmol), potassium acetate (9.8 g, 100.0 mmol) and 1 , 4-dioxane (, 120 mL) and [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (1.8 g, 2.5 mmol). The reaction liquid was heated to reflux at 110° C. for 3 hours under the protection of nitrogen gas. Cool to room temperature, distill off the solvent under reduced pressure, dissolve the residue with ethyl acetate (200 mL), filter to remove solid impurities, wash the filtrate with water (60 mL) and saturated brine (60 mL), dry over sodium sulfate, and filter. The filtrate was spin-dried, and the crude product was separated by silica gel column chromatography (petroleum ether: ethyl acetate volume ratio = 10:1) to obtain a yellow solid, Compound 1 (13.0 g, 45.9 mmol, 92%). 1 H NMR (300 MHz, CDCl 3 ): 1.35 (s, 12 H), 7.54 (d, J = 6.0 Hz, 1 H),7.89 (d, J = 6.0 Hz, 1 H), 8.10 (s, 1 H);
[0012] Step 2:
...
Embodiment 2
[0014] Embodiment 2: the first step reaction temperature is 90°C, the reaction time is 4 hours, the second step reaction temperature is 80°C, and the reaction time is 3 hours; the rest are the same as in Example 1.
Embodiment 3
[0015] Embodiment 3: the first step reaction temperature is 130°C, the reaction time is 2 hours, the second step reaction temperature is 130°C, and the reaction time is 1 hour; the rest are the same as in Example 1.
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