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Process for production of aromatic compounds meetings

Foreign code F110005487
File No. K05606WO
Posted date Sep 6, 2011
Country United States of America
Application number 58855205
Gazette No. 20070123734
Gazette No. 7781599
Date of filing Feb 10, 2005
Gazette Date May 31, 2007
Gazette Date Aug 24, 2010
International application number JP2005002529
International publication number WO2005075384
Date of international filing Feb 10, 2005
Date of international publication Aug 18, 2005
Priority data
  • P2004-033941 (Feb 10, 2004) JP
  • P2004-282578 (Sep 28, 2004) JP
  • 2005WO-JP02529 (Feb 10, 2005) WO
Title Process for production of aromatic compounds meetings
Abstract (US7781599)
A problem of the present invention is to provide an economical process with minimized toxicity for producing an aromatic compound having a variety of substituents such as various alkyl groups, and the problem is solved by a process for production of an aromatic compound represented by formula (1) below, which comprises reacting a compound represented by formula (2) below with an aromatic magnesium reagent represented by formula (3a) below in the presence of an iron catalyst and a diamine compound: wherein R is an optionally substituted hydrocarbon group or a C3-C10 saturated or unsaturated ring group; A is an optionally substituted C4-C20 aromatic group or an optionally substituted heteroaromatic group; X is a halogen atom or a sulfonic acid ester; and Y1 is bromine, iodine, chlorine or a carbanion ligand.
Scope of claims [claim1]
1. A process for production of an aromatic compound represented by formula (1) below:
R-A (1)
wherein, R is an optionally substituted hydrocarbon group or a C3-C10 saturated or unsaturated ring group, which ring may optionally be intervened by an oxygen atom or a group represented by formula -- N(B) -- (wherein B is a hydrogen atom, an optionally substituted C1-C10 hydrocarbon group or an optionally substituted C1-C10 alkoxycarbonyl group) and may optionally be substituted;
with the proviso that an aromatic group or a heteroaromatic group is excluded from R; and
A is an optionally substituted C4-C20 aromatic group or an optionally substituted heteroaromatic group, which comprises reacting a compound represented by formula (2) below:
R -- X (2)
wherein, R has the same significance as defined above, and X is a halogen atom or a sulfonic acid ester, with an aromatic magnesium reagent represented by formula (3a) below:
A-Mg -- Y1 (3a)
wherein A has the same significance as defined above and Y1 is bromine, iodine, chlorine or a carbanion ligand, in the presence of an iron catalyst and a diamine compound.
[claim2]
2. The process for production of an aromatic compound according to claim 1, wherein the iron catalyst is an iron salt or an iron complex.
[claim3]
3. The process for production of an aromatic compound according to claim 1, wherein the diamine compound is a bidentate ligand.
[claim4]
4. The process for production of an aromatic compound according to claim 1, wherein R is an optionally substituted primary alkyl group or an optionally substituted secondary alkyl group.
[claim5]
5. The process for production of an aromatic compound according to claim 1, wherein A is an optionally substituted C4-C20 aryl group.
[claim6]
6. A process for production of an aromatic compound represented by formula (1) below:
R-A (1)
wherein, R is an optionally substituted hydrocarbon group or a C3-C10 saturated or unsaturated ring group, which ring may optionally be intervened by an oxygen atom or a group represented by formula -- N(B) -- (wherein B is a hydrogen atom, an optionally substituted C1-C10 hydrocarbon group or an optionally substituted C1-C10 alkoxycarbonyl group) and may optionally be substituted;
with the proviso that an aromatic group or a heteroaromatic group is excluded from R; and
A is an optionally substituted C4-C20 aromatic group or an optionally substituted heteroaromatic group, which comprises:
a step of reacting an aromatic magnesium reagent represented by formula (3a) below:
A-Mg -- Y1 (3a)
wherein A has the same significance as defined above and Y1 is bromine, iodine, chlorine or a carbanion ligand, with a zinc compound represented by formula (4b) below:
Z3 -- Zn -- Z4 (4b)
wherein each of Z3 and Z4, which may be the same or different, independently represents bromine, iodine, chlorine, fluorine or a trifluoromethanesulfonyl group, in the presence of a diamine compound to give the reaction mixture; and
a step of reacting the reaction mixture with a compound represented by formula (2) below:
R -- X (2)
wherein R has the same significance as defined above and X is a halogen atom or a sulfonic acid ester, in the presence of an iron catalyst.
[claim7]
7. The process for production of an aromatic compound according to claim 6, wherein the iron catalyst is an iron salt or an iron complex.
[claim8]
8. The process for production of an aromatic compound according to claim 6, wherein the diamine compound is a bidentate ligand.
[claim9]
9. The process for production of an aromatic compound according to claim 6, wherein R is an optionally substituted primary alkyl group or an optionally substituted secondary alkyl group.
[claim10]
10. The process for production of an aromatic compound according to claim 6, wherein A is an optionally substituted C4-C20 aryl group.
[claim11]
11. A process for production of an aromatic compound represented by formula (1) below:
R-A (1)
wherein, R is an optionally substituted hydrocarbon group or a C3-C10 saturated or unsaturated ring group, which ring may optionally be intervened by an oxygen atom or a group represented by formula -- N(B) -- (wherein B is a hydrogen atom, an optionally substituted C1-C10 hydrocarbon group or an optionally substituted C1-C10 alkoxycarbonyl group) and may optionally be substituted;
with the proviso that an aromatic group or a heteroaromatic group is excluded from R; and
A is an optionally substituted C4-C20 aromatic group or an optionally substituted heteroaromatic group, which comprises:
a step of reacting an aromatic lithium reagent represented by formula (3c) below:
A-Li (3c)
wherein A has the same significance as defined above, with a zinc compound represented by formula (4b) below:
Z3 -- Zn -- Z4 (4b)
wherein each of Z3 and Z4, which may be the same or different, independently represents bromine, iodine or chlorine, in the presence of a diamine compound and then reacting with a Lewis acid metal compound containing at least one metal selected from magnesium, titanium, zirconium, hafnium, gallium and aluminum to give the reaction mixture, and
a step of reacting the reaction mixture with a compound represented by formula (2) below:
R -- X (2)
wherein R has the same significance as defined above and X is a halogen atom or a sulfonic acid ester, in the presence of an iron catalyst.
[claim12]
12. The process for production of an aromatic compound according to claim 11, wherein the iron catalyst is an iron salt or an iron complex.
[claim13]
13. The process for production of an aromatic compound according to claim 11, wherein the diamine compound is a bidentate ligand.
[claim14]
14. The process for production of an aromatic compound according to claim 11, wherein R is an optionally substituted primary alkyl group or an optionally substituted secondary alkyl group.
[claim15]
15. The process for production of an aromatic compound according to claim 11, wherein A is an optionally substituted C4-C20 aryl group.
[claim16]
16. The process for production of an aromatic compound according to claim 11, wherein the Lewis acid metal compound is a metal compound represented by formula (4c) below:
M(Z1)n (4c)
wherein M is magnesium, titanium, zirconium, hafnium, gallium or aluminum; each of Z1, which may be the same or different, independently represents bromine, iodine, chlorine or a carbanion ligand; and n is an integer of 2 to 4.
[claim17]
17. A process for production of an aromatic compound represented by formula (1) below:
R-A (1)
wherein, R is an optionally substituted hydrocarbon group or a C3-C10 saturated or unsaturated ring group, which ring may optionally be intervened by an oxygen atom or a group represented by formula -- N(B) -- (wherein B is a hydrogen atom, an optionally substituted C1-C10 hydrocarbon group or an optionally substituted C1-C10 alkoxycarbonyl group) and may optionally be substituted;
with the proviso that an aromatic group or a heteroaromatic group is excluded from R; and
A is an optionally substituted C4-C20 aromatic group or an optionally substituted heteroaromatic group, which comprises:
a step of reacting an aromatic zinc reagent represented by formula (3b) below:
A-Zn -- Y2 (3b)
wherein A has the same significance as defined above and Y2 is bromine, iodine or chlorine, with a magnesium compound represented by formula (4a) below:
Z1 -- Mg -- Z2 (4a)
wherein Z1 is a carbanion ligand and Z2 is bromine, iodine or chlorine] in the presence of a diamine compound to give the reaction mixture; and
a step of reacting the reaction mixture with a compound represented by formula (2) below:
R -- X (2)
wherein R has the same significance as defined above and X is a halogen atom or a sulfonic acid ester, in the presence of an iron catalyst.
[claim18]
18. The process for production of an aromatic compound according to claim 17, wherein the iron catalyst is an iron salt or an iron complex.
[claim19]
19. The process for production of an aromatic compound according to claim 17, wherein the diamine compound is a bidentate ligand.
[claim20]
20. The process for production of an aromatic compound according to claim 17, wherein R is an optionally substituted primary alkyl group or an optionally substituted secondary alkyl group.
[claim21]
21. The process for production of an aromatic compound according to claim 17, wherein A is an optionally substituted C4-C20 aryl group.
  • Inventor, and Inventor/Applicant
  • NAKAMURA MASAHARU
  • NAKAMURA EIICHI
  • MATSUO KEIKO
  • ITO SHINGO
  • JAPAN SCIENCE AND TECHNOLOGY AGENCY
IPC(International Patent Classification)
Reference ( R and D project ) PRESTO Synthesis and Control AREA
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