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Process for production of aromatic compounds 新技術説明会

外国特許コード F110005487
整理番号 K05606WO
掲載日 2011年9月6日
出願国 アメリカ合衆国
出願番号 58855205
公報番号 20070123734
公報番号 7781599
出願日 平成17年2月10日(2005.2.10)
公報発行日 平成19年5月31日(2007.5.31)
公報発行日 平成22年8月24日(2010.8.24)
国際出願番号 JP2005002529
国際公開番号 WO2005075384
国際出願日 平成17年2月10日(2005.2.10)
国際公開日 平成17年8月18日(2005.8.18)
優先権データ
  • 特願2004-033941 (2004.2.10) JP
  • 特願2004-282578 (2004.9.28) JP
  • 2005WO-JP02529 (2005.2.10) WO
発明の名称 (英語) Process for production of aromatic compounds 新技術説明会
発明の概要(英語) (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.
特許請求の範囲(英語) [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.
  • 発明者/出願人(英語)
  • NAKAMURA MASAHARU
  • NAKAMURA EIICHI
  • MATSUO KEIKO
  • ITO SHINGO
  • JAPAN SCIENCE AND TECHNOLOGY AGENCY
国際特許分類(IPC)
参考情報 (研究プロジェクト等) PRESTO Synthesis and Control AREA
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