Method for producing nitro compound

Patent metadata

Field	Value
Publication number	US-9561998-B2
Application number	US-201415107872-A
Country	US
Kind code	B2
Filing date	Dec 15, 2014
Priority date	Dec 26, 2013
Publication date	Feb 7, 2017
Grant date	Feb 7, 2017

Abstract

A nitro compound represented by formula (1) which is a raw material for producing a compound represented by formula (7) can be produced by reacting at least one type selected from the group consisting of a compound represented by formula (2), a compound represented by formula (3), and a compound represented by formula (3′) with a compound represented by formula (4). [In the formula, R 1 , R 2 , R 3 , and R 4 are each independently a hydrogen atom, etc., X 1 and X 2 are each independently a chlorine atom, etc., R 6 , R 7 , R 8 , and R 9 are a hydrogen atom, etc., provided that X 1 , X 2 , R 6 , R 7 , R 8 , and R 9 are not all the same, X 3 , X 4 , and X 5 are a halogen atom, R 10 is a nitro group, etc., R 5 is an alkyl group having 1 to 12 carbon atoms, etc., and M is an alkali metal atom.]

First claim

The invention claimed is:

1. A method for producing a nitro compound of formula (1):

wherein R 1 , R 2 , R 3 and R 4 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms optionally having a halogen atom or atoms, a cycloalkyl group having 3 to 6 carbon atoms, a halogen atom, an alkoxy group having 1 to 6 carbon atoms, an alkylthio group having 1 to 6 carbon atoms, an alkylamino group having 1 to 6 carbon atoms or an aryl group having 6 to 12 carbon atoms, and R 5 represents an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms or an alkenyl group having 2 to 6 carbon atoms, comprising a step of reacting a compound of formula (2):

wherein R 1 , R 2 , R 3 and R 4 have the same meanings as above,
at least one selected from the group consisting of a compound of formula (3):

wherein X 1 and X 2 each independently represent a chlorine atom, a bromine atom or an iodine atom, R 6 , R 7 , R 8 and R 9 each independently represent a halogen atom, an alkyl group having 1 to 6 carbon atoms optionally having a halogen atom or atoms, an alkenyl group having 2 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkoxycarbonyl group having 2 to 6 carbon atoms, a hydrogen atom or a cyano group, provided that X 1 , X 2 , R 6 , R 7 , R 8 and R 9 are not all the same, and R 7 and R 9 may be bonded each other to form a ring together with the carbon atoms to which they are bonded,
and a compound of formula (3′):

wherein X 3 , X 4 and X 5 represent a halogen atom, and R 10 represents a hydrogen atom, a nitro group, a halogen atom, an alkyl group having 1 to 6 carbon atoms optionally having a halogen atom or atoms, an alkoxy group having 1 to 6 carbon atoms or an aryl group having 6 to 12 carbon atoms,
and a compound of formula (4):
R 5 —OM  (4)

wherein R 5 has the same meaning as above, and M represents an alkali metal atom.

2. The method for producing a nitro compound according to claim 1 comprising a step of reacting the compound of formula (2), the compound of formula (3), and the compound of formula (4).

3. A method for producing a nitro compound represented by formula (1):

wherein R 1 , R 2 , R 3 and R 4 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms optionally having a halogen atom or atoms, a cycloalkyl group having 3 to 6 carbon atoms, a halogen atom, an alkoxy group having 1 to 6 carbon atoms, an alkylthio group having 1 to 6 carbon atoms, an alkylamino group having 1 to 6 carbon atoms or an aryl group having 6 to 12 carbon atoms, and R 5 represents an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms or an alkenyl group having 2 to 6 carbon atoms, comprising a step of reacting a compound of formula (5):
R 5 —OH  (5)

wherein R 5 has the same meaning as above,
a compound of formula (6):
M-OH  (6)

wherein M represents an alkali metal atom,
a compound of formula (2):

wherein R 1 , R 2 , R 3 and R 4 have the same meaning as above,
and at least one selected from the group consisting of a compound of formula (3):

wherein X 1 and X 2 each independently represent a chlorine atom, a bromine atom or an iodine atom, R 6 , R 7 , R 8 and R 9 each independently represent a halogen atom, an alkyl group having 1 to 6 carbon atoms optionally having a halogen atom or atoms, an alkenyl group having 2 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkoxycarbonyl group having 2 to 6 carbon atoms, a hydrogen atom or a cyano group, provided that X 1 , X 2 , R 6 , R 7 , R 8 and R 9 are not all the same, and R 7 and R 9 may be bonded each other to form a ring together with the carbon atoms to which they are bonded,
and a compound of formula (3′):

wherein X 3 , X 4 and X 5 represent a halogen atom, and R 10 represents a hydrogen atom, a nitro group, a halogen atom, an alkyl group having 1 to 6 carbon atoms optionally having a halogen atom or atoms, an alkoxy group having 1 to 6 carbon atoms or an aryl group having 6 to 12 carbon atoms.

4. The method for producing a nitro compound according to claim 3 comprising a step of reacting the compound of formula (5), the compound of formula (6), the compound of formula (2), and the compound of formula (3).

5. The production method according to claim 4 , wherein X 1 and X 2 are the same.

6. The production method according to claim 4 , wherein the compound of formula (3) is 1,2-dibromo-1,1,2,2-tetrachloroethane or 1,2-dibromo-1,1,2,2-tetrafluoroethane.

7. The method for producing a nitro compound according to claim 1 comprising a step of reacting the compound of formula (2), the compound of formula (3′), and the compound of formula (4).

8. The method for producing a nitro compound according to claim 3 comprising a step of reacting the compound of formula (5), the compound of formula (6), the compound of formula (2), and the compound of formula (3′).

9. The method for producing a nitro compound according to claim 7 , wherein R 10 is a halogen atom.

10. The method for producing a nitro compound according to claim 7 wherein the compound of formula (3′) is tetrabromomethane or bromotrichloromethane.

11. A method for producing a compound of formula (7):

wherein R 1 , R 2 , R 3 , R 4 and R 5 have the same meanings as above,
comprising obtaining a nitro compound of formula (1) by the production method as defined in claim 1 , and reducing the nitro compound of formula (1).

12. A nitro compound of formula (8):

wherein R 11 represents an alkyl group having 1 to 3 carbon atoms or a cycloalkyl group having 3 to 4 carbon atoms, and R 51 represents an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms or an alkenyl group having 2 to 6 carbon atoms.

13. The nitro compound according to claim 12 , wherein R 11 is a methyl group, and R 51 is an alkyl group having 1 to 6 carbon atoms.

14. The nitro compound according to claim 12 , wherein R 11 is a methyl group, and R 51 is a methyl group or an ethyl group.

Assignees

• Sumitomo Chemical Co

Inventors

• Yoshimoto Yuya
• Toriumi Tatsuya
• Nagashima yuta

Classifications

• C07C213/02

  by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups · CPC title

• C07C205/34

  having nitro groups bound to carbon atoms of six-membered aromatic rings and etherified hydroxy groups bound to acyclic carbon atoms of the carbon skeleton · CPC title

• C07C201/12 Primary

  by reactions not involving the formation of nitro groups · CPC title

• C07C217/76

  having amino groups bound to carbon atoms of six-membered aromatic rings and etherified hydroxy groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton · CPC title