Preparation method of 4-(alkyl-3-ene)-( fluoro)benzene derivative
A technology of biphenyl and methyl, which is applied in the field of preparation of 4--(fluoro)benzene derivatives, can solve the problems of long reaction steps and low product yield, achieve low cost, high yield, and overcome long reaction steps Effect
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[0041] The invention provides a preparation method of 4-(alkyl-3-ene)-(fluoro)benzene derivatives. First, the raw material compound I or III is made into a lithium reagent (i.e. compound II or IV), and then the lithium reagent and the compound Reaction VII yields 4-alkyl-3-ene-(fluoro)benzene derivatives. The specific process is as follows:
[0042] Step 1: Dissolve compound I (or III) in an ether solvent, drop alkyllithium into the solution of compound I (or Ш) at low temperature (-80 °C ~ -40 °C) for reaction, and keep warm for a period of time (0.5~3 hours), obtain compound II (or IV), and the reaction equation is:
[0043] or,
[0044]
[0045] Wherein, the molar ratio of the alkyllithium to the raw material compound I (or III) is 1:1-2:1;
[0046] In each structural formula of above-mentioned reaction equation, Ak is H or C 1 ~C 7 Any one of straight-chain alkyl groups, A is cyclohexyl ring or oxygen-containing heterocycle, n=0, 1 or 2, m=0, 1 or 2, n+m is 1 or ...
Embodiment 1
[0054]Preparation of 4-(3-buten-1-yl)-2'-fluoro-4″-(trans-4-methylcyclohexyl)-1,1’:4’,1″-terphenyl
[0055] Install a thermometer, mechanical stirring, and constant pressure dropping funnel on the 2L three-necked flask, then add 107.4g (0.3mol) 4-methyl-2'-fluoro-4″-(trans-4-methylcyclohexyl)- 1,1': 4',1″-terphenyl, 48.7gTMEDA, 400mL diethyl ether, stirred and cooled to -80°C, then added 136mL (0.3mol) n-butyllithium dropwise, after the dropwise addition, kept warm for 0.5 hours, in 23.0 g of allyl chloride was added dropwise at a temperature of -80°C, and then kept at a temperature of -80°C for 0.5 hour, and the reaction was completed.
[0056] Add dropwise 700g of 10% dilute hydrochloric acid solution to the product in the previous step, stir, separate layers, add a small amount of toluene dropwise to extract the aqueous phase, combine the organic phases, wash with water until neutral, concentrate to obtain 110g of crude product, and distill under reduced pressure and mix to...
Embodiment 2
[0058] Preparation of 5-heptyl-2-(4'-pentyl-3-en-biphenyl-4-yl)-[1,3]-dioxane
[0059] Install a thermometer, mechanical stirring, and a constant pressure dropping funnel on the 2L three-necked flask, and then add 176g (0.5mol) of 5-heptyl-2-(4'-methyl-biphenyl-4-yl)-[1, 3]-dioxane, 87gTMEDA, 500mL anisole, stirred and cooled to -60°C, then added dropwise 577mL (0.75mol) sec-butyllithium, after the dropwise addition, kept warm for 1 hour, at -60°C 90.5 g of croton chloride (1 mol) was added dropwise at low temperature, and then kept at -60°C for 1 hour to complete the reaction.
[0060] Add 1200g of 10% dilute hydrochloric acid solution dropwise to the product in the previous step, stir, separate layers, add a small amount of toluene dropwise to extract the aqueous phase, combine the organic phases, wash with water until neutral, concentrate to obtain 191g of crude product, and distill under reduced pressure and mix toluene / absolute ethanol The solvent recrystallized to obtai...
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