Substituted p-trifluoromethyl phenyl ether compound and its prepn and application
A technology of trifluoromethyl phenyl ether and compounds, which is applied in the field of substituted p-trifluoromethyl phenyl ether compounds, and can solve the problems that trifluoromethyl phenyl ether compounds are not specifically disclosed.
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example 1
[0063] Example 1: Preparation of Compound 1
[0064]
[0065] At room temperature, the mixture containing 0.8 g of anhydrous potassium carbonate, 0.39 g of (II-1), 0.4 g of (III-1) in 20 ml of N,N-dimethylformamide was heated under reflux and stirred for 5 hours, and the The reaction mixture was poured into ice water, extracted three times with ethyl acetate, the combined extracts were washed three times with saturated brine, dried, filtered, and concentrated under reduced pressure to obtain a light yellow solid as a crude product. Column chromatography with a mixture of ethyl acetate and petroleum ether (1:8) gave 0.51 g of the title compound, melting at 104-106°C. Yield 70.5%.
[0066] NMR data ( 1 HNMR, 300MHz, internal standard TMS, solvent CDCl 3 )as follows:
[0067] δppm 3.71(3H, s), 3.83(3H, s), 5.12(2H, s), 6.89(1H, d), 7.20(1H, t), 7.35(3H, m), 7.53(1H, m), 7.62 (2H, s).
example 2
[0068] Example 2: Preparation of Compound 4
[0069]
[0070] At room temperature, the mixture containing 0.8 g of anhydrous potassium carbonate, 0.39 g of (II-1), 0.42 g of (III-2) in 20 ml of N,N-dimethylformamide was heated under reflux and stirred for 5 hours, and the The reaction mixture was poured into ice water, extracted three times with ethyl acetate, the combined extracts were washed three times with saturated brine, dried, filtered, and concentrated under reduced pressure to obtain a light yellow solid as a crude product. Column chromatography with a mixture of ethyl acetate and petroleum ether (1:8) gave 0.53 g of the title compound with a melting point of 115-116°C. Yield 73.2%.
[0071] NMR data ( 1 HNMR, 300MHz, internal standard TMS, solvent CDCl 3 )as follows:
[0072] δppm 3.88(3H, s), 4.04(3H, s), 5.09(2H, s), 6.93(1H, d), 7.22(1H, d), 7.45(3H, m), 7.58(1H, d), 7.63 (1H, s).
example 3
[0073] Example 3: Preparation of Compound 7
[0074]
[0075] 0.60 g of compound 4 and an aqueous solution of methylamine with twice the molar ratio were stirred overnight at room temperature in 50 ml of tetrahydrofuran, concentrated and then extracted twice with ethyl acetate. The combined extracts were washed with water for three times and then washed twice with saturated brine. After drying, filtration and concentration, 0.53 g of the title compound was obtained, with a melting point of 92-94°C. Yield 88.5%.
[0076] NMR data ( 1 HNMR, 300MHz, internal standard TMS, solvent CDCl 3 )as follows:
[0077] δppm 2.92(3H, s), 3.92(3H, s), 5.12(2H, s), 6.95(1H, d), 7.24(1H, m), 7.42(3H, m), 7.54(1H, d), 7.62 (1H, s).
[0078] Other compounds were synthesized according to the above method.
[0079]The NMR data of the general formula I compound shown in part table 1 ( 1 HNMR, 300MHz, internal standard TMS, solvent CDCl 3 )as follows:
[0080] Compound 10: oily substance....
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