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One-pot method for preparing 2-bromo-9,9-diphenylfluorene

A technology of diphenylfluorene and phenyl, which is applied in the field of organic synthesis, can solve the problems of high cost of trifluoromethanesulfonic acid, influence on reaction yield, and low yield, and achieve simplified post-treatment process, reliable process, and simple operation Effect

Active Publication Date: 2015-11-25
HENAN BUSINESS SCI RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The cost of trifluoromethanesulfonic acid as a dehydrating agent is high, and the system is heterogeneous, so the yield is not high; using sulfuric acid as a dehydrating agent, the cost is low, but there are many by-products, which affect the reaction yield

Method used

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  • One-pot method for preparing 2-bromo-9,9-diphenylfluorene
  • One-pot method for preparing 2-bromo-9,9-diphenylfluorene

Examples

Experimental program
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Effect test

Embodiment 1

[0025] One-pot preparation of 2-bromo-9,9-diphenylfluorene, including the following steps:

[0026] (1) ;

[0027] (2) .

[0028] The specific operation of step (1) is as follows: a) firstly take 23 mmol of thionyl chloride and mix with 10 mmol of 2-bromo-9-phenyl-fluoren-9-ol; b) then take 35 mmol of thionyl chloride and heat it to 60 ° C, and then 0.5 In h, the mixed solution of step a) was added dropwise to it; c) the chlorination reaction was completed after the temperature was raised and refluxed for 3 h;

[0029] The specific operation of step (2) is: cooling the system after the chlorination reaction, adding 8.5mmol copper benzenesulfonate, then heating up to 40°C, adding 15mmol benzene dropwise within 0.5h, continuing to heat up to 55°C and reacting for 5h Finally, the copper benzenesulfonate was removed by filtration, and the filtrate was concentrated under reduced pressure to obtain 2-bromo-9,9-diphenylfluorene with a yield of 95.7%.

Embodiment 2

[0031] In the present embodiment, the copper benzene sulfonate will be added and replaced with copper p-toluene sulfonate, other are the same as in Example 1, and the final yield is 97.5%.

Embodiment 3

[0033] 2-Bromo-9,9-diphenylfluorene was prepared by one-pot method, and the reaction formula was the same as that in Example 1.

[0034] Include the following steps:

[0035] The specific operation of step (1) is as follows: a) firstly take 35 mmol of phosphorus trichloride and mix with 10 mmol of 2-bromo-9-phenyl-fluoren-9-ol; b) then take 53 mmol of phosphorus trichloride and heat to 70 ℃, and then 1h The mixed solution of step a) is added dropwise into it; c) the chlorination reaction ends after the temperature rises and refluxes for 5 hours;

[0036] The specific operation of step (2) is: cooling the system after the chlorination reaction, adding 11 mmol copper p-toluenesulfonate, then heating up to 48 ° C, adding 22 mmol benzene dropwise within 0.5 h, and continuing to heat up to 60 ° C for 7 h. , and finally the copper p-toluenesulfonate was removed by filtration, and the filtrate was concentrated under reduced pressure to obtain 2-bromo-9,9-diphenylfluorene with a yiel...

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Abstract

The invention relates to a one-pot method for preparing 2-bromo-9,9-diphenylfluorene and belongs to the technical field of organic synthesis. The method comprises steps shown in the specification. The reaction can be finished in one reactor, particularly for a chlorination reaction, intermediate products are not required to be separated out, a subsequent reaction of replacement of chlorine atoms with benzene rings is performed after a system reactant and a catalyst are directly added, the whole operation is simple, and the technology is reliable and suitable for enlargement; besides, by means of the used catalyst, side reactions can be effectively reduced, the product yield is increased to be higher than 90%, meanwhile, separation can be realized through filtration after the reaction due to the fact that the catalyst is a solid catalyst, and the after-treatment process is simplified.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to the preparation of 2-bromo-9,9-diphenylfluorene by a one-pot method. Background technique [0002] Fluorene and its derivatives have the characteristics of a large conjugated system in the molecule, a rigid planar biphenyl structure, a wide energy gap, a high luminous efficiency, and easy modification of the structure, making them widely used in electroluminescent materials. , solar cell materials and other fields have a wide range of applications. [0003] Dehydration reaction of tertiary alcohols with aromatic rings, Chang, ShunLi et al. (Journal of Organic Chemistry, 75(12), 4004-4013, 2010), Kim, BokYeong et al. (Repub.KoreanKongkaeTaehoKongbo, 2010006072), Seok, Hwan et al. (U.S.Pat.20090200928) and Lee, Seok-Jong et al. (U.S.Pat. 20040157084) respectively proposed trifluoromethanesulfonic acid and sulfuric acid as dehydrating agents. Trifluoromethane...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C25/22C07C17/266
Inventor 王永王法云张立攀张亚勋任钊郭青照罗蓓蓓李栋
Owner HENAN BUSINESS SCI RES INST
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