Method for conducting halogenated trifluoromethylation reaction on alkene
A technology for halogenating trifluoromethyl and trifluoromethyl groups, applied in chemical instruments and methods, organic chemistry, halogenated hydrocarbon preparation, etc., can solve the problems of high cost, harsh reaction conditions, difficult separation and purification, etc., and achieve low cost , the reaction is simple, the effect of mild conditions
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Embodiment 1
[0023] Example 1 Chlorinated trifluoromethylation reaction of cyclic α, β-unsaturated amides
[0024] Under the protection of argon, 1-methyl-3-methylene-2-pyrazolone (222mg, 2mmol), 1-(trifluoromethyl)-1,2-phenyliodyl-3(1H )-ketone (948mg, 3mmol), copper bromide (4.5mg, 0.02mmol), Molecular sieves (10 mg) were dissolved in 20 mL of dry chloroform and stirred well. Thionyl chloride (238 mg, 2 mmol) was added dropwise to the reaction system at room temperature and stirred for 8 hours. After the reaction was completed, 10 mL of 2mol / L dilute hydrochloric acid was added to quench the reaction. The liquid was separated, and the aqueous phase was extracted once with 5 mL of ethyl acetate. Combine the organic phases, concentrate the organic phases with a rotary evaporator, and use column chromatography to separate the concentrated solution. The eluent used for column chromatography separation is ethyl acetate:petroleum ether=1:10 (volume ratio). The column chromatography efflue...
Embodiment 2
[0030] Example 2 Chlorinated trifluoromethylation reaction of chain α, β-unsaturated amides
[0031] Under argon protection, N,N-diethylmethacrylamide (282mg, 2mmol), 1-(trifluoromethyl)-1,2-phenyliodyl-3(1H)-one (1264mg, 4mmol), copper bromide (4.5mg, 0.02mmol), Molecular sieves (10 mg) were dissolved in 20 mL of dry dioxane and stirred well. Oxalyl chloride (305 mg, 2.4 mmol) was added dropwise to the reaction system at room temperature and stirred for 8 hours. After the reaction was completed, 10 mL of 2mol / L dilute hydrochloric acid was added to quench the reaction. The liquid was separated, and the aqueous phase was extracted once with 5 mL of ethyl acetate. Combine the organic phases, concentrate the organic phases with a rotary evaporator, and use column chromatography to separate the concentrated solution. The eluent used for column chromatography separation is ethyl acetate:petroleum ether=1:10 (volume ratio). The column chromatography effluent was concentrated b...
Embodiment 3
[0037] The chlorotrifluoromethylation reaction of embodiment 3 linear olefins
[0038] Under argon protection, 1-dodecene (337mg, 2mmol), 1-(trifluoromethyl)-1,2-phenyliodide-3(1H)-one (1264mg, 4mmol), bromide Copper (4.5mg, 0.02mmol), Molecular sieves (10 mg) were dissolved in 20 mL of dry dioxane and stirred well. Oxalyl chloride (305 mg, 2.4 mmol) was added dropwise to the reaction system at room temperature and stirred for 8 hours. After the reaction was completed, 10 mL of 2mol / L dilute hydrochloric acid was added to quench the reaction. The liquid was separated, and the aqueous phase was extracted once with 5 mL of ethyl acetate. Combine the organic phases, concentrate the organic phases with a rotary evaporator, and use column chromatography to separate the concentrated solution. The eluent used for column chromatography separation is ethyl acetate:petroleum ether=1:50 (volume ratio). The column chromatography effluent was concentrated by rotary evaporation and suck...
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