Synthetic method of loxoprofen
A synthesis method and compound technology, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of long synthesis route of compound I, reduced yield of compound I, poor activity of compound VI, etc., and achieve convenient operation. , the effect of reducing impurities and short synthesis route
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[0079] The preparation of the compound VIII used can be operated with reference to the prior art: Synthesis, 1991, 2, 112. The preparation steps are as follows:
[0080] Dissolve 192g of tert-butyl phenylacetate in 1L of tetrahydrofuran, control at -40°C, add 500mL of 2NLDA (lithium diisopropylamide) in tetrahydrofuran dropwise to the reaction system, and continue stirring at -40°C for 1h , then add 170g methyl iodide dropwise, warm up to room temperature after dropping, and continue to stir for 1h. After removing the solvent tetrahydrofuran under reduced pressure, add 2L dichloromethane, then wash twice with 500mL water, and the organic layer obtained by liquid separation is dichloromethane The solution layer was concentrated after drying, and the obtained crude product was distilled under reduced pressure, and the fraction (1.5 mmHg) at 75 to 80 degrees was collected to obtain 181 g of a very light yellow liquid, which was compound VIII, which could be directly used in the sy...
Embodiment 1
[0084] A kind of synthetic method of loxoprofen, concrete steps are as follows:
[0085] (1), the synthesis of intermediate compound IX
[0086] Add 69g of compound VIII, 300mL of dichloromethane and 55g of anhydrous aluminum trichloride in the reaction flask and then control the temperature in the reaction flask to be about 5°C and add 50mL of dichloromethane solution containing 53.5g of compound VII into the reaction flask, then Raise the temperature to 30°C with stirring and react until no gas is released to obtain a reaction liquid, then cool the obtained reaction liquid to -5~0°C, add 1L of 2N hydrochloric acid aqueous solution to the reaction liquid with stirring, and then heat up to Stirring was continued at 10°C for 4h, and then the layers were separated to obtain an aqueous phase and an organic phase;
[0087] After the obtained aqueous phase was extracted once with 200 mL of dichloromethane, the above-mentioned organic phases were combined, and the resulting combina...
Embodiment 2
[0096] A kind of synthetic method of loxoprofen, concrete steps are as follows:
[0097] (1), the synthesis of intermediate compound IX
[0098] Add 69g of compound VIII, 400mL of hexafluorobenzene and 88g of anhydrous aluminum trichloride into the reaction flask, then control the temperature in the reaction flask to about 5°C, and add 53.5g of compound VII in 100mL of hexafluorobenzene solution into the reaction flask , then heated up to 55°C under stirring conditions and reacted until no gas was released to obtain a reaction solution, cooled the resulting reaction solution to -5~0°C, added 1.2L of 2N hydrochloric acid aqueous solution to the reaction solution under stirring conditions, and then raised the temperature Stirring was continued at 10°C for 3.5h, and then the layers were separated to obtain an aqueous phase and an organic phase;
[0099] After the obtained aqueous layer was extracted once with 200 mL of hexafluorobenzene, the organic layers obtained above were co...
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