Method for producing a substituted benzoic acid compound

Patent metadata

Field	Value
Publication number	US-9580401-B2
Application number	US-201314398246-A
Country	US
Kind code	B2
Filing date	Apr 30, 2013
Priority date	May 8, 2012
Publication date	Feb 28, 2017
Grant date	Feb 28, 2017

Abstract

To provide an industrial method for producing a substituted benzoic acid compound useful as an intermediate of pharmaceutical and agricultural chemicals with high purity and high yield.
A compound represented by the formula (II):

(wherein Q is a 5- or 6-membered saturated heterocyclic group (the heterocyclic group may be substituted by alkyl) containing one or two of at least one type of hetero atom selected from the group consisting of an oxygen atom and a sulfur atom, or dialkoxymethyl, T is trifluoromethyl, nitro, cyano, —SOA 1 , —SO 2 A 1 , —PO(OA 1 )(OA 2 ), —COA 1 , —CO 2 A 1 or —CONA 1 A 2 , each of A 1 and A 2 which are independent of each other, is a hydrogen atom, alkyl or haloalkyl, X is halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, dialkylaminosulfonyl, di(haloalkyl)aminosulfonyl, nitro or cyano, Y is a chlorine atom, a bromine atom or an iodine atom, and n is an integer of from 1 to 6), carbon monoxide and a compound represented by the formula R—OH (wherein R is alkyl) are reacted, followed by hydrolysis to obtain a compound represented by the formula (I):

wherein Q, T, X and n are as defined above.

First claim

The invention claimed is:

1. A method for producing a compound represented by the following formula (I):

wherein Q is a 5- or 6-membered saturated heterocyclic group, the heterocyclic group can be substituted by alkyl, containing one or two of at least one hetero atom selected from the group consisting of an oxygen atom and a sulfur atom, or Q is dialkoxymethyl;
T is trifluoromethyl, nitro, cyano, —SOA 1 , —SO 2 A 1 , —PO(OA 1 )(OA 2 ), —COA 1 , —CO 2 A 1 or —CONA 1 A 2 , and each of A 1 and A 2 which are independent of each other, is a hydrogen atom, alkyl or haloalkyl;
X is halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, dialkylaminosulfonyl, di(haloalkyl)aminosulfonyl, nitro or cyano; and
n is an integer of from 1 to 6;
which comprises reacting a compound represented by the following formula (II):

wherein Y is a chlorine atom, a bromine atom or an iodine atom;
with carbon monoxide and a compound represented by the formula R—OH, wherein R is alkyl, to produce a compound represented by the following formula (III):

and hydrolyzing the compound of the formula (III).

2. The production method according to claim 1 , wherein the reaction of the compound represented by the above formula (II), carbon monoxide and the compound represented by the formula R—OH is carried out in the presence of a base and a transition metal catalyst, and further as the case requires, in the presence of a solvent.

3. The production method according to claim 1 , wherein the hydrolysis is carried out in the presence of a base, and then the reaction mixture is acidified with an acid.

4. A compound represented by the formula (II):

wherein Q is a 5- or 6-membered saturated heterocyclic group the heterocyclic group can be substituted by alkyl, containing one or two of at least one hetero atom selected from the group consisting of an oxygen atom and a sulfur atom, or Q is dialkoxymethyl;
T is trifluoromethyl, nitro, cyano, —SOA 1 , —SO 2 A 1 , —PO(OA 1 )(OA 2 ), —COA 1 , —CO 2 A 1 or —CONA 1 A 2 , and each of A 1 and A 2 which are independent of each other, is a hydrogen atom, alkyl or haloalkyl;
X is halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, dialkylaminosulfonyl, di(haloalkyl)aminosulfonyl, nitro or cyano; and
Y is a chlorine atom, a bromine atom or an iodine atom; and
n is an integer of from 1 to 6.

5. The compound according to claim 4 , wherein Q is dioxolan-2-yl, T is methylsulfonyl, X is a chlorine atom, Y is a bromine atom, and n is 2.

6. A compound represented by the following formula (IV):

wherein T is methylsulfonyl, X is a chlorine atom, and Y is a bromine atom.

7. The production method according to claim 2 , wherein the hydrolysis is carried out in the presence of a base, and then the reaction mixture is acidified with an acid.

8. The production method according to claim 1 , wherein Q is dioxolan-2-yl, T is methylsulfonyl, X is a chlorine atom, Y is a bromine atom, and n is 2.

Assignees

• Ishihara Sangyo Kaisha

Inventors

• Jonishi Hisayoshi
• Okamoto Tomohiro
• Adachi Norio
• Isogai Akihiko
• Jukurogi Tatsuya
• Konishi Hideaki
• Fukui Fumihiro

Classifications

• C07D317/26

  Radicals substituted by doubly bound oxygen or sulfur atoms or by two such atoms singly bound to the same carbon atom · CPC title

• C07D317/22

  etherified · CPC title

• C07D319/06 Primary

  not condensed with other rings · CPC title

• C07C317/22

  with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton · CPC title