JP2000508680A - 2―置換7―ハロインデンと合成方法 - Google Patents
2―置換7―ハロインデンと合成方法Info
- Publication number
- JP2000508680A JP2000508680A JP10533255A JP53325598A JP2000508680A JP 2000508680 A JP2000508680 A JP 2000508680A JP 10533255 A JP10533255 A JP 10533255A JP 53325598 A JP53325598 A JP 53325598A JP 2000508680 A JP2000508680 A JP 2000508680A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- reacting
- produce
- reaction mixture
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F17/00—Metallocenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/32—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen
- C07C1/325—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen the hetero-atom being a metal atom
- C07C1/326—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen the hetero-atom being a metal atom the hetero-atom being a magnesium atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/18—Polycyclic aromatic halogenated hydrocarbons
- C07C25/22—Polycyclic aromatic halogenated hydrocarbons with condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.式: [式中、Xはハロゲンであり、R1は炭素数1〜10のアルキル基である] を有する化合物。 2.式: を有する化合物。 3.式: を有する化合物。 4.Xが塩素、臭素又はヨウ素である、請求項1記載の化合物。 5.式Iを有する化合物を、ArMgX[式中、Arは任意のアリール基で あり、Xはハロゲンである]と反応させて、式IIを有する化合物を製造するこ とを含む方法。 6.Arがフェニル、ナフチル又は9−フルオレニル基である、請求項5記 載の方法。 7.Xが塩素又は臭素又はヨウ素である、請求項5又は6に記載の方法。 8.R1がメチル、エチル、プロピル、イソプロピル、ブチル、イソブチル 、ヘキシル、イソヘキシル、オクチル又はイソオクチル基である、請求項5又は 6に記載の方法。 9.式Iを有する化合物の合成方法であって、次の工程: (i)マロン酸ジエステルをアルカリ金属水素化物及び2−ハロベンジルハラ イドと反応させて、式IVを有する化合物を形成する工程と; (ii)式IVを有する前記化合物をケン化して、式Vを有する化合物を形成す る工程と; (iii)式Vを有する前記化合物を式VIIを有する化合物に転化させる工程 と; (iv)式VIIを有する前記化合物をSOCl2と反応させて、式VIIIを 有する化合物を製造する工程と; (v)式VIIIを有する前記化合物を塩化アルミニウムと反応させて、化合 物IXを製造する工程と; (vi)式IXを有する前記化合物をホウ水素化ナトリウムと反応させて、式X を有する化合物を製造する工程と; (vii)式Xを有する前記化合物をパラトルエンスルホン酸と反応させて、式 Iを有する前記化合物を製造する工程と を含む上記合成方法。 10.(i)工程(i)の前記マロン酸ジエステルが式IIIを有し、 (ii)工程(i)のアルカリ金属水素化物が水素化ナトリウムであり、工程(i) のハロベンジルハライドが2−クロロベンジルクロリドである、請求項9記載の 方法。 11.(i)炭素数1〜10の脂肪酸のアルカリ金属塩をアルカリ金属水素化 物と反応させて、中間体化合物を含有する第1反応混合物を製造する工程と:(i i)前記工程(i)反応混合物に2−ハロベンジルハライドを混合して、前記 中間体化合物を式IVを有する化合物を製造する工程と を含む方法。 12.式:[式中、R1は炭素数1〜10の直鎖又は分枝鎖アルキル基である] を有する化合物をナフチルマグネシウムブロミドと反応させて、式: を有する化合物を含有する反応混合物を製造する方法。 13.式: を有する化合物中のR1がメチル又はエチルである、請求項12記載の方法。 14.7−クロロ−2−メチルインデンとナフチルマグネシウムブロミドと を反応させて、7−ナフチル−2−メチルインデンを含有する反応混合物を製造 することを含む方法。 15.前記7−ナフチル−2−メチルインデンを前記反応混合物から分離す る、請求項14記載の方法。 16.(i)式Iを有する化合物をArMgX[式中、Arが任意のアリール 基であり、Xがハロゲンである]と反応させて、式IIを有する化合物を製造す る工程と; (ii)工程(i)で製造された前記式II化合物を式:[式中、Q1とQ2は同じ又は異なる式II化合物であり、Yはアルキル基であり 、MはIV族金属であり、Zはハロゲンである] を有する化合物に転化させる工程と を含む方法。 17.Yがメチルであり、Zが塩素である、請求項16記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/795,019 | 1997-02-05 | ||
US08/795,019 US5789634A (en) | 1997-02-05 | 1997-02-05 | Coupling reactions of 2-substituted, 7-haloindenes with aryl substituents to produce metallocene catalyst intermediates |
PCT/US1998/002345 WO1998033752A1 (en) | 1997-02-05 | 1998-02-05 | 2-substituted 7-haloindenes and methods for synthesizing |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2000508680A true JP2000508680A (ja) | 2000-07-11 |
JP2000508680A5 JP2000508680A5 (ja) | 2005-11-24 |
JP4372230B2 JP4372230B2 (ja) | 2009-11-25 |
Family
ID=25164410
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP53325598A Expired - Fee Related JP4372230B2 (ja) | 1997-02-05 | 1998-02-05 | 2―置換7―ハロインデンと合成方法 |
Country Status (7)
Country | Link |
---|---|
US (1) | US5789634A (ja) |
EP (1) | EP0920406B1 (ja) |
JP (1) | JP4372230B2 (ja) |
AU (1) | AU6148898A (ja) |
CA (1) | CA2250740C (ja) |
DE (1) | DE69825960T2 (ja) |
WO (1) | WO1998033752A1 (ja) |
Families Citing this family (33)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6075171A (en) * | 1997-02-05 | 2000-06-13 | Boulder Scientific Company | 2-substituted 7-haloindenes and methods for synthesizing |
US6465700B1 (en) * | 1997-02-05 | 2002-10-15 | Boulder Scientific Company | Coupling reactions of 2-substituted, 7-haloindenes with aryl substituents to produce metallocene catalyst ligands |
US6586625B1 (en) * | 2000-05-08 | 2003-07-01 | Boulder Scientific Company | Synthesis of 2-halobenzyl alkanoic acid |
US6380122B1 (en) | 2000-06-30 | 2002-04-30 | Exxonmobil Chemical Patents Inc. | Metallocene compositions |
US6380120B1 (en) | 2000-06-30 | 2002-04-30 | Exxonmobil Chemical Patents Inc. | Metallocene compositions |
US6380121B1 (en) | 2000-06-30 | 2002-04-30 | Exxonmobil Chemical Patents Inc. | Metallocene compositions |
US6380334B1 (en) | 2000-06-30 | 2002-04-30 | Exxonmobil Chemical Patents Inc. | Metallocene compositions |
US6399723B1 (en) | 2000-06-30 | 2002-06-04 | Exxonmobil Chemical Patents Inc. | Metallocene compositions |
US6376409B1 (en) | 2000-06-30 | 2002-04-23 | Exxonmobil Chemical Patents Inc. | Metallocene compositions |
US6380123B1 (en) | 2000-06-30 | 2002-04-30 | Exxonmobil Chemical Patents Inc. | Metallocene compositions |
US6380330B1 (en) | 2000-06-30 | 2002-04-30 | Exxonmobil Chemical Patents Inc. | Metallocene compositions |
US7122498B2 (en) * | 2000-06-30 | 2006-10-17 | Exxonmobil Chemical Patents Inc. | Metallocenes and catalyst compositions derived therefrom |
US6380331B1 (en) | 2000-06-30 | 2002-04-30 | Exxonmobil Chemical Patents Inc. | Metallocene compositions |
US6376407B1 (en) | 2000-06-30 | 2002-04-23 | Exxonmobil Chemical Patents Inc. | Metallocene compositions |
US6376408B1 (en) | 2000-06-30 | 2002-04-23 | Exxonmobil Chemical Patents Inc. | Metallocene compositions |
US6376412B1 (en) | 2000-06-30 | 2002-04-23 | Exxonmobil Chemical Patents Inc. | Metallocene compositions |
US6376411B1 (en) | 2000-06-30 | 2002-04-23 | Exxonmobil Chemical Patents Inc. | Metallocene compositions |
US6380124B1 (en) | 2000-06-30 | 2002-04-30 | Exxonmobil Chemical Patents Inc. | Metallocene compositions |
US6376627B1 (en) | 2000-06-30 | 2002-04-23 | Exxonmobil Chemical Patents Inc. | Metallocene compositions |
US6376413B1 (en) | 2000-06-30 | 2002-04-23 | Exxonmobil Chemical Patents Inc. | Metallocene compositions |
US6870016B1 (en) * | 2000-06-30 | 2005-03-22 | Exxonmobil Chemical Patents Inc. | Polymerization process and polymer composition |
US6414095B1 (en) | 2000-06-30 | 2002-07-02 | Exxon Mobil Chemical Patents Inc. | Metallocene compositions |
US6376410B1 (en) | 2000-06-30 | 2002-04-23 | Exxonmobil Chemical Patents Inc. | Metallocene compositions |
JP2005522406A (ja) | 2001-06-29 | 2005-07-28 | エクソンモービル・ケミカル・パテンツ・インク | メタロセン及び該メタロセン由来の触媒組成物 |
DE10152989A1 (de) * | 2001-10-26 | 2003-05-08 | Bayer Ag | Komplexe N-heterocyslischer Carbene und ihre Verwendung |
DE10214938A1 (de) * | 2002-04-04 | 2003-10-16 | Merck Patent Gmbh | Fluorierte Indene und 1,7-Dihydroindacene mit negativem delta epsilon |
JP2005529865A (ja) * | 2002-04-10 | 2005-10-06 | バーゼル、ポリオレフィン、ゲゼルシャフト、ミット、ベシュレンクテル、ハフツング | インデン置換体の製造方法 |
US7205427B2 (en) * | 2002-06-04 | 2007-04-17 | Boulder Scientific Company | Cross-coupling synthesis of alkyl (dialkylphenyl) indenes |
EP1554233A1 (en) * | 2002-10-22 | 2005-07-20 | Basell Polyolefine GmbH | Preparation of substituted indenes |
DE10249325A1 (de) * | 2002-10-22 | 2004-05-06 | Basell Polyolefine Gmbh | Verfahren zur Herstellung von substituierten Indenen |
US7105467B2 (en) * | 2003-07-08 | 2006-09-12 | Pharmacore, Inc. | Nickel catalyzed cross-coupling reactions between organomagnesium compounds and anisole derivatives |
DE10358082A1 (de) * | 2003-12-10 | 2005-07-14 | Basell Polyolefine Gmbh | Organübergangsmetallverbindung, Bscyclopentadienyligandsystem, Katalysatorsystem und Hertellung von Polyolefinen |
US7910783B2 (en) | 2005-12-14 | 2011-03-22 | Exxonmobil Chemical Patents Inc. | Preparation of substituted bridged indenyl and related ligands |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2953609A (en) * | 1958-04-29 | 1960-09-20 | American Oil Co | Preparation of substituted tetrahydro-indenoindene |
US5059572A (en) * | 1989-10-31 | 1991-10-22 | Shell Oil Company | Catalyst and process for coupling organometallic reagents with aryl or vinylic halides |
TW294669B (ja) * | 1992-06-27 | 1997-01-01 | Hoechst Ag | |
DE4303634B4 (de) * | 1993-02-09 | 2006-06-14 | Merck Patent Gmbh | Indan-Derivate |
-
1997
- 1997-02-05 US US08/795,019 patent/US5789634A/en not_active Expired - Lifetime
-
1998
- 1998-02-05 CA CA002250740A patent/CA2250740C/en not_active Expired - Fee Related
- 1998-02-05 EP EP98906206A patent/EP0920406B1/en not_active Expired - Lifetime
- 1998-02-05 DE DE69825960T patent/DE69825960T2/de not_active Expired - Lifetime
- 1998-02-05 AU AU61488/98A patent/AU6148898A/en not_active Abandoned
- 1998-02-05 WO PCT/US1998/002345 patent/WO1998033752A1/en active IP Right Grant
- 1998-02-05 JP JP53325598A patent/JP4372230B2/ja not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
EP0920406A1 (en) | 1999-06-09 |
EP0920406B1 (en) | 2004-09-01 |
CA2250740C (en) | 2008-08-05 |
CA2250740A1 (en) | 1998-08-06 |
JP4372230B2 (ja) | 2009-11-25 |
AU6148898A (en) | 1998-08-25 |
DE69825960D1 (de) | 2004-10-07 |
DE69825960T2 (de) | 2005-09-08 |
WO1998033752A1 (en) | 1998-08-06 |
US5789634A (en) | 1998-08-04 |
EP0920406A4 (ja) | 1999-06-09 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP4372230B2 (ja) | 2―置換7―ハロインデンと合成方法 | |
EP0512554B1 (en) | Method for making cyclopentadiene type compounds | |
KR100283824B1 (ko) | 아릴-치환된 인데닐 유도체를 리간드로서 함유하는 메탈로센, 이를 사용한 올레핀 중합체의 제조방법 및 촉매로서의 이의 용도 | |
US6465700B1 (en) | Coupling reactions of 2-substituted, 7-haloindenes with aryl substituents to produce metallocene catalyst ligands | |
JPH0859722A (ja) | 非晶質のプロピレンのポリマーの製造方法 | |
JP3815814B2 (ja) | 橋状メタロセン化合物の製造法 | |
US5393911A (en) | Cyclopentadiene type compounds and method for making | |
JP2004531529A (ja) | モノハライドまたはジハライドメタロセン化合物の製造方法 | |
US6075171A (en) | 2-substituted 7-haloindenes and methods for synthesizing | |
EP0920403B1 (en) | Process for preparing cyclopentadienyl compounds | |
WO2000040528A1 (en) | Pentafulvene synthesis | |
JP2005529865A (ja) | インデン置換体の製造方法 | |
JP2017527525A (ja) | インデンの合成のための方法 | |
JP4346193B2 (ja) | ベンゼン誘導体の製造方法 | |
EP0854876A2 (en) | Production of bridged metallocene complexes and intermediates therefor | |
JPH08245670A (ja) | 1,3−ジ置換シクロペンタジエニル−配位子との遷移金属錯体の製造方法 | |
JP2006503885A (ja) | 置換インデンの製造方法 | |
TW201125872A (en) | New metallocene compounds, catalysts comprising them, process for producing an olefin polymer by use of the catalysts, and olefin homo- and copolymers |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20050201 |
|
A521 | Written amendment |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20050404 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20070911 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20071210 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20080128 |
|
A521 | Written amendment |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20080111 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20080304 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20080603 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20080714 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20080703 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20080811 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20080801 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20080908 |
|
A521 | Written amendment |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20080827 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20090519 |
|
A521 | Written amendment |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20090527 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20090811 |
|
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20090902 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20120911 Year of fee payment: 3 |
|
R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130911 Year of fee payment: 4 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
LAPS | Cancellation because of no payment of annual fees |