Preparation of 4-bromo-2-(4′-ethoxyphenyl)-1-chlorobenzene

US11565990B2 · kind B2 · utility

Assignee

• WISDOM PHARMACEUTICAL CO., LTD · CN

Inventors

• Lin Hu · Nantong, CN
• Tao Xu · Suzhou, CN
• Xiaolong Qiu · Nantong, CN
• Xiaoyue Li · Nantong, CN
• Zhiwei Zuo · Plainsboro, US
• Wenbo Liu · Shanghai, CN
• Lingling Chu · Nantong, CN
• Ximeng Yuan · Nantong, CN
• Ping ZOU · Nantong, CN

Key dates

• Filing date: Jun 9, 2021
• Grant date: Jan 31, 2023
• Expiry date: Jun 9, 2041

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C45/46
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

A more environmentally friendly synthesis method of 4-bromo-2-(4′-ethoxyphenyl)-1-chlorobenzene with simplified steps provides a more effective synthetic strategy for producing key intermediates of SGLT-2 inhibitors such as dapagliflozin, sotagliflozin, and ertugliflozin. In the presence of trifluoroacetic anhydride, 5-bromo-2-chlorobenzoic acid and phenetole are selected to complete a direct acylation reaction under the catalysis of boron trifluoride diethyl etherate, and triethylsilane is added thereinto without treatment for one-pot reaction to obtain a target compound 4-bromo-2-(4′-ethoxyphenyl)-1-chlorobenzene.