Preparation method of ethylene compound containing fluorine and trifluoromethyl groups at the same time
A technology of trifluoromethyl and trifluoromethyl sources, applied in the preparation of carbon-based compounds, the preparation of organic compounds, organic chemical methods and other directions, can solve the problems of severe conditions, unfavorable large-scale production, etc., and achieves wide sources and costs. Low, high-yield effects
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Embodiment 1
[0027] Example 1: A method for simultaneously introducing fluorine and trifluoromethyl groups on terminal alkynes to prepare vinyl compounds, using the following process steps:
[0028] Put copper trifluoromethyl compound 1 (0.1mmol, 45mg), triethylamine (0.2mmol, 20mg) and p-chlorophenylacetylene (2a, 0.1mmol, 13.7mg) into a 25mL reaction tube, vacuumize and fill with nitrogen (three times). DMF (1 mL) was injected with a syringe under nitrogen protection. Stir in an oil bath at 100°C for 12 hours, cool to room temperature, filter, add the reaction solution and 20 mL of water to the extraction funnel, then add 25 mL of dichloromethane for extraction, then take the organic layer and add a small amount of silica gel to spin dry column chromatography to obtain Product 3a as colorless oil (68% yield).
[0029] The reaction process of above-mentioned steps is shown in following formula (1):
[0030]
[0031] The NMR data of product 3a are as follows:
[0032] 1 H NMR (400M...
Embodiment 2
[0033] Embodiment 2: A method for simultaneously introducing fluorine and trifluoromethyl groups on terminal alkynes to prepare vinyl compounds, using the following process steps:
[0034] Put copper trifluoromethyl compound 1 (0.10mmol, 45mg), triethylamine (0.2mmol, 20mg) and p-methoxyphenylacetylene (2b, 0.1mmol, 13mg) into a 25mL reaction tube, vacuumize and fill with nitrogen (three times). DMF (1 mL) was injected with a syringe under nitrogen protection. Stir in an oil bath at 100°C for 12 hours, cool to room temperature, filter, add the reaction solution and 20 mL of water to the extraction funnel, then add 25 mL of dichloromethane for extraction, then take the organic layer and add a small amount of silica gel to spin dry column chromatography to obtain Product 3b as colorless oil (61% yield).
[0035] The reaction process of above-mentioned steps is shown in following formula (2):
[0036]
[0037] The NMR data of product 3b are as follows:
[0038] 1 H NMR (4...
Embodiment 3
[0039] Embodiment 3: A method for simultaneously introducing fluorine and trifluoromethyl groups on terminal alkynes to prepare vinyl compounds, using the following process steps:
[0040] Put copper trifluoromethyl compound 1 (0.10mmol, 45mg), triethylamine (0.5mmol, 75mg) and p-carbonylphenylacetylene (2c, 0.1mmol, 15mg) into a 25mL reaction tube, vacuumize and fill with nitrogen ( three times). DMF (1 mL) was injected with a syringe under nitrogen protection. Stir in an oil bath at 100°C for 12 hours, cool to room temperature, filter, add the reaction solution and 20 mL of water to the extraction funnel, then add 25 mL of dichloromethane for extraction, then take the organic layer and add a small amount of silica gel to spin dry column chromatography to obtain The white solid product 3c is shown as:
[0041] The reaction process of above-mentioned steps is shown in following formula (3):
[0042]
[0043] The NMR data of product 3c are as follows:
[0044] 1 H NMR (40...
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