Method for synthesizing multi-substituted 1-naphthol

[0019] Example 1

[0020] Under the protection of nitrogen, a solution of p-bromophenylzinc iodide in tetrahydrofuran (2.4 ml, 0.5M, 1.2 mmol) and xylene (3 ml) were successively added to the reaction tube, placed in an oil bath at 140 degrees Celsius, and the The original solvent tetrahydrofuran of the zinc reagent was distilled off. After half an hour of distillation, a xylene solution (2 mL) of ethyl 2-methyl-4-phenyl-2,3-butadienoate (0.0414 g, 0.2 mmol) was added to the reaction tube with stirring, After reacting at 140 degrees Celsius for 0.5 hours, add 1 ml of saturated ammonium chloride solution dropwise to quench the reaction, return to room temperature naturally and drop to zero, extract with ether, wash with 5% hydrochloric acid, saturated sodium bicarbonate, and saturated saline each time , dried over anhydrous sodium sulfate. Filtration, concentration, and flash column chromatography gave 0.0523 g of 2-methyl-3-(4'-bromophenyl)-1-naphthol with a yield of 82%. The

[0021] Example 2

[0022] According to the method described in Example 1, the difference is that the substrate and reagent used are: 2-methyl-4,4-diphenyl-2,3-butadienoic acid ethyl ester (0.0554 grams, 0.2 mmol) , a n-hexane solution of diethylzinc (0.7 ml, 0.88M, 0.6 mmol) to obtain 0.0486 g of 2-methyl 4-ethyl-3-phenyl-1-naphthol with a yield of 93%. The product is a white solid: Solid; m.p.85.2-88.1°C (hexane / ethyl acetate); 1 H NMR (300MHz, CDCl 3 )δ8.10(d, J=8.4Hz, 1H), 7.50-7.35(m, 4H), 7.29-7.17(m, 4H), 5.22(s, 1H), 2.56(q, J=7.5Hz, 2H ), 2.42(s, 3H), 1.01(t, J=7.5Hz, 3H); 13 C NMR (CDCl 3 , 75MHz) δ148.1, 140.3, 139.3, 132.3, 131.2, 130.7, 128.1, 126.8, 126.5, 125.3, 124.4, 122.5, 120.5, 115.7, 24.5, 15.0, 11.8; MS (EI) m / z (%) 262 (M + , 100); IR(KBr, cm -1 )3407, 3069, 2963, 2930, 2871, 1622, 1592, 1573, 1503, 1442, 1376, 1318, 1287, 1195, 1164, 1099, 1069, 1034; HRMS Calcd for C 19 h 18 O(M + ): 262.1358, Found: 262.1358.

[0023] Example 3

[0024] According to the method described in Example 1, the difference is that the solvent used is 1,3,5-trimethylbenzene; the temperature is 160 degrees Celsius; the substrate and reagent are: 2-methyl-2,4-diphenyl-2, Ethyl 3-butadienoate (0.0554 g, 0.2 mmol), tetrahydrofuran solution of p-fluorophenylzinc iodide (2.4 ml, 0.5M, 1.2 mmol), gave 2-methyl-3-(4' -Fluorophenyl)-4-phenyl-1-naphthol 0.0460 g, yield 70%. The product is a white solid: Solid; m.p.176.3-177.5°C (hexane / ethyl acetate); 1 H NMR (300MHz, CDCl 3 )δ8.22(d, J=8.4Hz, 1H), 7.54-7.44(m, 2H), 7.38-7.30(m, 1H), 7.24-7.15(m, 3H), 7.07-7.02(m, 2H) , 7.00-6.93(m, 2H), 6.90-6.82(m, 2H), 5.26(s, 1H), 2.14(s, 3H); 13 CNMR (CDCl 3, 75MHz) δ161.2 (d, J=243.8Hz), 148.1, 139.4, 139.0, 136.5 (d, J=3.5Hz), 131.9, 131.8, 131.7 (d, J=7.4Hz), 131.4, 127.5, 126.8 , 126.2, 125.8, 125.3, 123.4, 120.8, 115.3, 114.5 (d, J=20.4Hz), 13.8; 19 F NMR (CDCl 3 , 282Hz) δ-116.3; MS (EI) m / z (%) 328 (M + , 100); IR