A synthesis method of 2-bromo-9,9-diphenylfluorene taking 1-bromotriphenylmethane as raw material

CN122145268APending Publication Date: 2026-06-05ZHONGWEI NAT ENG RES CTR FOR COKING TECH CO LTD
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
ZHONGWEI NAT ENG RES CTR FOR COKING TECH CO LTD
Filing Date
2026-01-16
Publication Date
2026-06-05

AI Technical Summary

Technical Problem

Existing methods for synthesizing 2-bromo-9,9-diphenylfluorene suffer from low yields, demanding conditions, hazardous operations, and poor environmental performance, making it difficult to meet the requirements for high efficiency, safety, and stability.

Method used

Using 1-bromotriphenylmethane as a raw material, 2-bromo-9,9-diphenylfluorene was synthesized in three steps via metal-catalyzed coupling (Suzuki reaction) and intramolecular cyclization reaction, including the formation of triphenylmethylpinacol boronic acid ester, coupling with 4-bromo-2-iodophenol, and the final intramolecular cyclization reaction.

Benefits of technology

It achieves an efficient and safe synthetic route, avoids harsh conditions, improves selectivity and overall yield, reduces waste liquid treatment pressure, and is suitable for laboratory and pilot-scale amplification.

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Abstract

The application belongs to the technical field of organic synthesis, and particularly relates to a synthesis method of 2-bromo-9,9-diphenylfluorene taking 1-bromotriphenylmethane as raw material. 1-bromotriphenylmethane and 4-bromo-2-iodophenol are taken as raw material, and a three-step reaction is carried out. Firstly, 1-bromotriphenylmethane and pinacol diboron perform boron esterification under the action of a palladium catalyst to generate triphenylmethyl pinacol borate. Then, the borate and 4-bromo-2-iodophenol perform coupling reaction under the action of a palladium catalyst to generate 4-bromo-2-(triphenylmethyl)phenol. Finally, the intermediate performs intramolecular ring closure reaction under the action of an acid to obtain the target product 2-bromo-9,9-diphenylfluorene. The route design of the application is novel, the harsh conditions and low selectivity of traditional Friedel-Crafts alkylation reaction are avoided, the reaction condition is mild, and the selectivity is high. A new way is provided for preparing the important photoelectric material intermediate.
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