Liquid crystal compound containing difluoromethoxy bridged bonds, and preparation method and application thereof
A technology of difluoromethoxy bridges and liquid crystal compounds, which is applied in the field of liquid crystal display materials, can solve the problems that compounds do not have application performance, and achieve good application prospects
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Embodiment 1
[0051] 1) Add 17.4g of 3,5-difluorophenylboronic acid, 18.5g of p-bromobenzaldehyde, 0.5g of tetrakis(triphenylphosphine)palladium, 50ml of toluene, 50ml of ethanol and 50ml of water into the reaction flask. Under nitrogen protection, reflux for 8 hours. After the reaction was completed, 16.5 g of compound N1 was obtained through extraction and purification. The reaction formula is as follows:
[0052]
[0053] 2) Add 120 mL of tetrahydrofuran to 40 g of bromoethane triphenylphosphine salt, lower the temperature to 0° C. under nitrogen protection, then add 12 g of potassium tert-butoxide and keep warm for 30 minutes. Then, a solution of 16.5 g of compound N1 + 50 mL of tetrahydrofuran was added dropwise, and the temperature was controlled at 0-5° C. during the dropwise addition. After the addition was complete, stir overnight at room temperature. After diluting with water, extracting with petroleum ether, purifying through a silica gel column, and evaporating the solvent...
Embodiment 2
[0062] 1) Compound N1 was prepared according to the method of Example 1).
[0063] 2) Add 51.3g of chloromethyl ether triphenylphosphine salt into 150mL of tetrahydrofuran, lower the temperature to 0°C under the protection of nitrogen, then add 16.8g of potassium tert-butoxide and keep warm for 30 minutes. Then, a solution prepared by 21.8g of intermediate M1+50mL of tetrahydrofuran was added dropwise, the temperature was controlled at 0-5°C during the dropwise addition, and the mixture was stirred overnight at room temperature after the addition. After diluting with water, extracting with petroleum ether, purifying through a silica gel column, and evaporating the solvent to dryness, 22.1 g of vinyl ether (N2) was obtained.
[0064] Add 22.1 g of enyl ether (M3) into 60 mL of dichloromethane, then add 30 mL of acetic acid and 10 g of 30% hydrochloric acid, and heat to reflux for 3 hours. Liquid separation, washing with water and neutralization treatment, and evaporation of th...
Embodiment 3
[0073]
[0074] In the reaction bottle, add 22g of compound S-1 (commercially available liquid crystal intermediate), 150ml of anhydrous tetrahydrofuran, lower the temperature to -80°C under nitrogen protection, add 0.11mol (2.5mol / L) of butyllithium dropwise, and finish adding -80 ℃ for 3 hours. The temperature was lowered to -90°C, and 30 g of difluorodibromomethane + 60 ml of tetrahydrofuran were added dropwise. After the addition, the temperature was naturally raised and stirred overnight. Add 200ml of water, use petroleum ether to extract and wash with water, dry and purify through a silica gel column to obtain about 30g of compound S-2, with an effective content of about 56%.
[0075] About 30g of compound S-2 was added in the reactor, 9g of 3,4,5-trifluorophenol (compound M3), 80ml of DMF, and 13.8g of potassium carbonate were added. Under nitrogen protection, keep warm at 75-80°C for 16 hours. Add water to the feed liquid and use toluene to extract, wash and dry ...
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