Process for producing 5-(3-cyanophenyl)-3-formylbenzoic acid compound

• US 20050014966A1
• Filed: 11/30/2001
• Published: 01/20/2005
• Est. Priority Date: 11/30/2001
• Status: Active Grant

• Current Assignee: Teijin Limited
• Original Assignee: Teijin Limited
• Inventors: Minoshima, Toru, Tabe, Masayasu
• Granted Patent: US 6,949,668 B2
• Time in Patent Office: Days
• US Class Current: 558/359
• CPC Class Codes: C07C 253/30 by reactions not involving the formation of cyano groups
• CPC Class Codes: C07C 255/57 containing cyano groups and carboxyl groups, other than cyano groups, bound to the carbon skeleton
• CPC Class Codes: C07C 51/353 by isomerisation; by change of size of the carbon skeleton
• CPC Class Codes: C07C 51/373 by introduction of functional groups containing oxygen only in doubly bound form
• CPC Class Codes: C07C 65/30 containing —CHO groups
• CPC Class Codes: C07F 5/025 Boronic and borinic acid compounds

Abstract

A 5-(3-cyanophenyl)-3-formylbenzoic acid compound of the formula (IV) is prepared by reacting a 5-bromo-3-(hydroxymethyl)benzoic acid compound of the formula (I) with manganese dioxide to provide a 5-bromo-3-formylbenzoic acid compound of the formula (II), and then reacting the resultant compound of the formula (II) with 3-cyanophenylboronic acid of the formula (III) in the presence of a palladium complex.
R is a H atom or a C₁-C₁₀ alkyl group.

Claims

1. A process for producing a 5-(3-cyanophenyl)-3-formylbenzoic acid compound comprising the steps of:

reacting a 5-bromo-(3-hydroxymethyl)benzoic acid compound represented by the formula (I);

in which formula (I), R represents a hydrogen atom or a linear or branched chain alkyl group having 1 to 10 carbon atoms, with manganese dioxide, to prepare a 5-bromo-3-formylbenzoic acid compound represented by the formula (II);

in which formula (II), R is as defined above; and

reacting the resultant 5-bromo-3-formylbenzoic acid compound with 3-cyanophenylboronic acid represented by the formula (III);

in the presence of a palladium complex, to prepare a 5-(3-cyanophenyl)-3-formylbenzoic acid compound represented by the formula (IV);

in which formula (IV), R is as defined above.

2. The process for producing a 5-(3-cyanophenyl)-3-formylbenzoic acid compound as claimed in claim 1, wherein the 3-cyanophenylboronic acid represented by the formula (III) is one prepared by reacting 3-formyl-phenylboronic acid represented by the formula (V):

3. The process for producing a 5-(3-cyanophenyl)-3-formylbenzoic acid compound as claimed in claim 2, wherein the 3-formylphenylboronic acid represented by the formula (V) is one prepared by reacting a 3-(dialkoxymethyl)bromobenzene represented by the formula (VI):

4. The process for producing a 5-(3-cyanophenyl)-3-formylbenzoic acid compound as claimed in claim 1, wherein the 5-bromo-3-(hydroxymethyl)benzoic acid compound represented by the formula (I) is one prepared by reacting a 5-bromoisophthalic acid compound represented by the formula (VII):

5. The process for producing a 5-(3-cyanophenyl)-3-formylbenzoic acid compound as claimed in claim 4, wherein the 5-bromo-3-(hydroxymethyl)benzoic acid compound prepared by the reaction of the 5-bromoisophthalic acid compound represented by the formula (VII) with sodium borohydride, is purified by using a mixed solvent comprising an alcohol and a benzene derivative.