Alkylation method of fluorine-containing aryl halid
An aryl halide and alkylation technology, which is applied in the field of alkylation of fluorine-containing aryl halides, can solve the problems of aldehydes and ketones affecting the reaction yield, multiple equipment and manpower, and long reaction steps, etc., to achieve product purity Excellent, reduced equipment and manpower occupation, and mild conditions
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[0048] The method for the alkylation of the fluorine-containing aryl halide I, that is, the preparation method of the compound of the formula V comprises the following steps:
[0049] 1) Grignard reagent formula III is prepared by reacting the compound of formula I structure as raw material and metal magnesium in an aprotic solvent, and the reaction equation is as follows:
[0050]
[0051] 2) the Grignard reagent of formula III is catalyzed by a transition metal salt, or under the joint catalysis of a transition metal salt and a ligand, with an alkyl halide R 1 -Hal' reacts to generate compound formula V:
[0052]
[0053] The method for the alkylation of the fluorine-containing aryl halide III, that is, the preparation method of the compound of the formula VI comprises the following steps:
[0054] 1) Grignard reagent formula IV is prepared by reacting the compound of formula II structure as raw material and metal magnesium in an aprotic solvent, and the reaction equa...
Embodiment 1
[0082] Preparation of 2,6-difluoro-4-propylphenisopropyl ether
[0083] (1) Under nitrogen protection, add 22.9g of magnesium chips, a little iodine grains and 150mL THF into a 2L four-necked bottle, first add 20g of 2,6-difluoro-4-bromophenylisopropyl ether, and start the reaction at about 50°C, After initiation, add a solution of 180g 2,6-difluoro-4-bromophenylisopropyl ether and 850mL THF dropwise at 50±3°C for about 1 hour, then keep stirring at 50°C for 1 hour after dropping, and monitor the reaction by GC. The conversion was over 99.0%.
[0084] (2) Add 167.2g of 1-bromopropane, 3.1g of copper chloride, 5.6g of phenanthroline and 400mL of tertiary methyl ether into another 2L four-necked bottle under the protection of nitrogen, and add step (1 ), the Grignard reagent prepared in ) was dropped in about 1.5 hours, stirred at 50°C for 1 hour after the drop, and the reaction endpoint was monitored by GC. Control the temperature of the system below 30°C and add a sufficient...
Embodiment 2
[0086] Preparation of 2,6-difluoro-4-(3-phenylpropyl)phenylbenzyl ether
[0087] (1) Under the protection of nitrogen, add 21.6g of magnesium chips, a little iodine grains and 100mL of methyl tetrahydrofuran into a 2L four-necked bottle, first add 30g of 2,6-difluoro-4-bromophenylbenzyl ether, and start the reaction at about 60°C After initiation, add dropwise a solution of 210g 2,6-difluoro-4-bromophenylbenzyl ether and 900mL methyl tetrahydrofuran to the system at 50±3°C for about 1 hour, then keep stirring at 60°C for 1 hour after dropping, and monitor the reaction by GC. The starting material has been converted over 99.0%.
[0088] (2) Under the protection of nitrogen, add 256.2g of 3-phenyl-1-bromopropane, 2.9g of ferric chloride, 6.8g of dppbz and 500mL of methyl tetrahydrofuran into another 2L four-necked bottle, and drop the steps at 70±3℃ The Grignard reagent prepared in (1) was dropped in about 1.5 hours, stirred at 70°C for 1 hour after the drop, and the reaction e...
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