Process for preparing highly pure formylphenylboronic acids

Abstract

A process for purifying formylphenylboronic acids of the formula (I) where the formyl function is located in the ortho, meta or para position relative to the boronic acid function, by dissolving the crude formylphenylboronic acids in an alkaline solvent having a pH in the range from 8 to 11 separating off the insoluble organic impurities and subsequently acidifying the alkaline boronic acid solution and separating off and working up the precipitated boronic acid. The crude formylphenylboronic acid is preferably dissolved in aqueous alkali metal or alkaline earth metal oxide, hydroxide, carbonate or phosphate solutions at temperatures in the range from 5 to 50° C. The formylphenylboronic acids obtained have a purity of ≧99% and are suitable as precursors for liquid-crystalline compounds, as liquid crystals or as constituents of liquid-crystalline mixtures or as pharmaceutical intermediates.

1 . A process for purifying formylphenylboronic acids of the formula (I)  
       
         
           
           
               
               
           
         
       
       where the formyl function is located in the ortho, meta or para position relative to the boronic acid function and R 1  to R 4  are each, independently of one another, hydrogen, C 1 -C 12 -alkyl, C 2 -C 12 -alkenyl, C 2 -C 12 -alkynyl, C 3 -C 12 -cycloalkyl, C 1 -C 12 -alkoxy, O-phenyl, O-benzyl, aryl, heteroaryl, fluorine, N(alkyl) 2 , N[Si(C 1 -C 4 -alkyl) 3 ] 2  or CF 3 , or R 1  and R 2 , and/or R 3  and R 4 , together form an aliphatic or aromatic ring, by dissolving the crude formylphenylboronic acids in an alkaline solvent having a pH in the range from 8 to 11, separating off the insoluble organic impurities and subsequently acidifying the alkaline boronic acid solution and separating off and working up the precipitated boronic acid.  
     
     
         2 . The process as claimed in  claim 1 , wherein the crude formylphenylboronic acid is dissolved in aqueous alkali metal or alkaline earth metal oxide, hydroxide, carbonate or phosphate solutions.  
     
     
         3 . The process as claimed in  claim 1 , wherein the purification is carried out temperatures in the range from 5 to 50° C.  
     
     
         4 . The process as claimed in  claim 1 , wherein the organic impurities are removed by adsorption on activated carbon or extraction with inert, water-immiscible solvents.  
     
     
         5 . The process as claimed in  claim 1 , wherein the formylphenylboronic acid obtained has a purity of ≧99%.  
     
     
         6 . A formylphenylboronic acid of the the formula (I) having a purity of ≧99%, obtainable by a process as claimed in  claim 1 .  
     
     
         7 . The use of a formylphenylboronic acid as claimed in  claim 6  as precursor for liquid-crystalline compounds, as liquid crystals or as a constituent of liquid-crystalline mixtures or as a pharmaceutical intermediate.  
     
     
         8 . The process as claimed in  claim 2 , wherein the purification is carried out temperatures in the range from 5 to 50° C.  
     
     
         9 . The process as claimed in  claim 2 , wherein the organic impurities are removed by adsorption on activated carbon or extraction with inert, water-immiscible solvents.  
     
     
         10 . The process as claimed in  claim 2 , wherein the formylphenylboronic acid obtained has a purity of ≧99%.  
     
     
         11 . A formylphenylboronic acid of the the formula (I) having a purity of ≧99%, obtainable by a process as claimed in  claim 2.