Process for the preparation of substituted phenylboronic acids

US6576789B1 · kind B1 · utility

Assignee

• Clariant Corporation · DE

Inventors

• Steffen Haber · Landau, DE
• Andreas Meudt · Hofheim, DE
• Stefan Scherer · Büttelborn, DE
• Frank Vollmueller · Mainz, DE

Key dates

• Filing date: Apr 20, 2000
• Grant date: Jun 10, 2003
• Expiry date: Apr 20, 2020

Classification

• Technology area (CPC Y): Emerging Cross-Sectional Technologies
• CPC primary: Y02P20/55
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Compounds of the formula (I) in whichQ1 and Q2 are each OH or form a trimeric boric anhydride, Z is CHO, CH2Y, X or a protected aldehyde group, and X is CN, COOH, COCl, CONH2 or C(OR)3, and Y is OH or NH2, and Z is in the o-, m- or p-position to the boronic acid radical,are prepared bya) reacting a compound of the formula (II)  with Mg in the presence of an anthracene compound and, if desired, a transition-metal halide and, if desired, an Mg halide or in the presence of a transition-metal halide and, if desired, an Mg halide, to give the corresponding arylmagnesium chloride,b) reacting the latter with a borate of the formula B(OR′)3 and hydrolyzing the product, with removal of the aldehyde protecting group,c) and, if desired, oxidizing or reducing the free aldehyde group.