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Synthetic method for 4,4'-dihalogenated-3,3'-dialkyl(alkoxyl) biphenyl compounds

A synthesis method and compound technology are applied in the field of synthesis of 4,4'-dihalogen substituted-3,3'-dialkylbiphenyl compounds, which can solve difficult scale production, harsh conditions, high price, etc. problem, to achieve the effect of mild reaction conditions, simple post-processing and low price

Inactive Publication Date: 2016-02-24
烟台九目化学股份有限公司
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  • Abstract
  • Description
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Problems solved by technology

[0005] The difficulty of this synthetic method is the synthesis of compound A and compound B: in the process of synthesizing A, because 4-nitro-2-methylbromobenzene contains nitro, it cannot be directly made into Grignard reagent, Grignard reagents need to be replaced when preparing Grignard reagents, but phenylmagnesium chloride Grignard reagents are difficult to prepare, and the reaction needs to be carried out in an ultra-low temperature environment, the conditions are harsh, and the yield is low (20%), so it is difficult to produce on a large scale , leading to expensive

Method used

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  • Synthetic method for 4,4'-dihalogenated-3,3'-dialkyl(alkoxyl) biphenyl compounds
  • Synthetic method for 4,4'-dihalogenated-3,3'-dialkyl(alkoxyl) biphenyl compounds
  • Synthetic method for 4,4'-dihalogenated-3,3'-dialkyl(alkoxyl) biphenyl compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 14

[0035] Example 14, Synthesis of 4'-dibromo(chloro / iodine)-3,3'-dimethylbiphenyl (G1-A~G1-C)

[0036]

[0037] Synthesis of 2,2'-dimethylhydroazobenzene (E1):

[0038] Dissolve 102.8g (0.75mol) of the raw material o-nitrotoluene in 700g of ethanol with a mass concentration of 95%, pour it into an autoclave, add 1.5g of 1,4-naphthoquinone, and then add 700g of a 50% mass concentration of sodium hydroxide solution , 1.5g sodium dodecylbenzenesulfonate and 1.5g Pd / C catalyst containing Pd0.8wt%, after replacing the air in the autoclave three times with nitrogen, then replace it with hydrogen three times, seal the autoclave, start stirring, and heat to React under the conditions of 30°C and 0.6MPa until the pressure of the autoclave no longer changes, cool down to 20-25°C, discharge the material, filter out the Pd / C catalyst and reuse it. The filtrate was separated into layers, the organic layer was taken, and the solvent was evaporated to dryness by rotary evaporation to obtai...

Embodiment 2

[0050] Example 2: Synthesis of 4,4'-dibromo(chloro / iodine)-3,3'-dimethoxybiphenyl (G2-A~G2-C)

[0051]

[0052] Synthesis of 2,2'-dimethoxyhydroazobenzene (E2):

[0053] Dissolve 114.8g (0.75mol) of the raw material o-nitromethoxybenzene in 600g of ethanol with a mass concentration of 95%, pour it into an autoclave, add 1.5g of 1,4-naphthoquinone, and then add 600g of hydrogen with a mass concentration of 50% Sodium oxide solution, 1.72g sodium dodecylbenzene sulfonate and 1.72g Pd / C catalyst containing Pd0.8wt%, nitrogen replacement autoclave inner air three times, then use hydrogen replacement three times, autoclave is sealed, start stirring, Heating to 35°C and 0.6MPa to react until the pressure of the autoclave no longer changes, then cool down to 20-25°C, discharge the material, filter out the Pd / C catalyst, and reuse it. The filtrate was separated into layers, the organic layer was taken, and the solvent was evaporated by rotary evaporation to obtain 85.4 g of solid ...

Embodiment 3

[0065] Example 3: Synthesis of 4,4'-diiodo(chloro / bromo)-3,3'-diethoxybiphenyl (G3A-G3C)

[0066]

[0067] Synthesis of 2,2'-diethoxyhydroazobenzene (E3):

[0068] Dissolve 125.7 g (0.75 mol) of raw material D3 o-nitroethoxybenzene in 817.05 g of ethanol with a mass concentration of 95%, pour it into an autoclave, add 1.5 g of 1,4-naphthoquinone, and then add 817.05 g of a mass concentration of 50 % sodium hydroxide solution, 1.9g sodium dodecylbenzenesulfonate and 1.9g containing the Pd / C catalyst of Pd0.8wt%, nitrogen replacement air three times, and then use hydrogen replacement three times, autoclave is sealed, open and stir, Heating to 35°C and 0.6MPa to react until the pressure of the autoclave no longer changes, then cooling down to 20-25°C, discharging, and filtering out the Pd / C catalyst for reuse. The filtrate was separated, the organic layer was taken, and the solvent was evaporated to dryness by rotary evaporation to obtain 96 g of solid 2,2'-diethoxyhydroazobe...

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Abstract

The invention relates to a synthetic method for 4,4'-dihalogenated-3,3'-dialkyl(alkoxyl) biphenyl compounds. The method employs o-nitro alkyl (alkoxyl) benzene as an initial raw material, 2,2'-dialkyl(alkoxyl) hydrazobenzene is prepared through catalysis hydrogenation in an alkaline environment, hydrochloric acid acidifying rearrangement is carried out, 4,4'-diamino-3,3'-dialkyl(alkoxyl) biphenyl is prepared, finally, a diazotization reaction is carried out and 4,4'-dihalogenated-3,3'-dialkyl(alkoxyl) biphenyl compounds are prepared. The synthetic method is advantaged by cheap and easily available raw materials, mild reaction conditions, simple operation, high safety coefficient, high yield and low cost.

Description

technical field [0001] The invention relates to a method for synthesizing 4,4'-dihalogen substituted-3,3'-diolk(oxy)biphenyl compounds, belonging to the field of chemical synthesis. Background technique [0002] 4,4'-dihalogen-substituted-3,3'-dioxylk(oxy)biphenyl compounds are an important class of fine chemical intermediates, used in OLED, OPC, photoresist materials, and even pharmaceutical intermediates It is widely used in synthesis, and the most representative compound of this type of compound is 4,4'-dihalogen substituted-3,3'-dimethylbiphenyl. [0003] The synthetic method of 4,4-dibromo-3,3'-dimethylbiphenyl disclosed in the literature is mainly the following method: [0004] [0005] The difficulty of this synthetic method is the synthesis of compound A and compound B: in the process of synthesizing A, because 4-nitro-2-methylbromobenzene contains nitro, it cannot be directly made into Grignard reagent, Grignard reagents need to be replaced when preparing Grign...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C25/18C07C17/093C07C43/225C07C41/22
CPCC07C17/093C07C41/22C07C209/54C07C213/02C07C241/02
Inventor 陈慕欣房平磊宋贺张世才万国君于发喜
Owner 烟台九目化学股份有限公司
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