Process for producing 5-(3-cyanophenyl)-3-formylbenzoic acid compound
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 C 1 -C 10 alkyl group.
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-formylphenylboronic acid represented by the formula (V):
with hydroxyamine hydrochloride.
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):
in which formula (VI), R 1 represents a linear or branched chain alkyl group having 1 to 4 carbon atoms, with magnesium metal to prepare an organic magnesium compound of the 3-(dialkoxymethyl)bromobenzene; and then further reacting the resultant organic magnesium compound with a trialkyl borate.
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):
in which formula (VII), R is as defined above, with sodium borohydride.
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.