Preparation method of novel 3-chlorocoumarin derivatives
A technology for chlorocoumarins and coumarins, which is applied in the field of preparation of novel 3-chlorocoumarins derivatives, can solve the problems of complexity, many side effects, low reaction yield and the like, and achieves good regioselectivity, The effect of low toxicity and easy availability of raw materials
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Embodiment 1
[0026] Synthesis of 3-chlorocoumarin:
[0027] Using coumarin as raw material, that is, R in formula Ⅰ 1 , R 2 are all H, where R 1 For any one of the 5-8 positions, the reaction formula is as follows:
[0028]
[0029] In a 25mL three-necked flask equipped with a stirrer, a thermometer and a reflux condenser, 20ml of organic solvent acetonitrile was added, followed by addition of coumarin (1mmol, 146mg), metal salt catalyst copper chloride CuCl 2 2H 2 O (4mmol, 684mg) and zinc chloride ZnCl 2 (1mmol, 136mg) and NCS (2mmol, 667.7mg), coumarin, cupric chloride, zinc chloride, NCS were dissolved in acetonitrile, stirred and refluxed at 82°C for 16h, cooled. Gained mixture carries out vacuum distillation (underpressure distillation condition is under 100~200mmHg vacuum degree, temperature 45~55 ℃) removes acetonitrile, quenches reaction with water, remaining gained material adds 50ml deionized water, extracts with 50ml ethyl acetate, takes The organic phase and the remai...
example 2
[0036] Synthesis of 3,4-dichlorocoumarin:
[0037] Using 4-chlorocoumarin as raw material, that is, R in formula Ⅰ 1 All H, R 2 is Cl, where R 1 For any one of the 5-8 positions, the reaction formula is as follows:
[0038]
[0039] In a 25mL three-necked flask equipped with a stirrer, a thermometer and a reflux condenser, 20ml of organic solvent acetonitrile was added, followed by addition of 4-chlorocoumarin (1mmol, 179.5mg), metal salt catalyst copper chloride CuCl 2 2H 2 O (2mmol, 342mg) and aluminum chloride AlCl 3 (2mmol, 267mg) and NCS (2mmol, 667.7mg), 4-chlorocoumarin, copper chloride, aluminum chloride, and NCS were dissolved in acetonitrile, stirred and refluxed at 82°C for 24h, and cooled. Gained mixture carries out vacuum distillation (underpressure distillation condition is under 100~200mmHg vacuum degree, temperature 45~55 ℃) removes acetonitrile, quenches reaction with water, remaining gained material adds 50ml deionized water, extracts with 50ml ethyl ...
example 3
[0046] Synthesis of 6-methyl-3-chlorocoumarin:
[0047] Using 6-methylcoumarin as raw material, that is, R in formula Ⅰ 1 is methyl (-CH 3 ), R 2 are all H, where R 1 On the 6-position of 6-methylcoumarin, its reaction formula is as follows:
[0048]
[0049] In a 25mL three-necked flask equipped with a stirrer, a thermometer and a reflux condenser, add 20ml of organic solvent 1,4-dioxane, then add 6-methylcoumarin (1mmol, 160.2mg), metal salt catalyst Copper Chloride CuCl 2 2H 2 O (2mmol, 342mg) and zinc chloride ZnCl 2 (1mmol, 136mg) and NCS (2mmol, 667.7mg), so that 6-methylcoumarin, copper chloride, zinc chloride, NCS dissolved in 1,4-dioxane, stirred at 200 ° C under reflux reaction 8h, cooling. The obtained mixture was subjected to vacuum distillation (the condition of vacuum distillation was 100-200 mmHg vacuum degree, temperature 65-75° C.) to remove 1,4-dioxane, quenched the reaction with water, and added 50 ml of deionized water to the remaining obtained s...
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