A kind of preparation method of 3-chlorocoumarin derivatives
A technology of chlorocoumarin and coumarin, which is applied in the field of preparation of 3-chlorocoumarin derivatives, can solve problems such as complexity, low reaction yield, and many side effects, and achieve good regioselectivity, raw material Easy to obtain, low toxicity effect
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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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