WO2008080993A3 - A method for preparation of substituted adamantylarylmagnesium halides - Google Patents
A method for preparation of substituted adamantylarylmagnesium halides Download PDFInfo
- Publication number
- WO2008080993A3 WO2008080993A3 PCT/EP2007/064648 EP2007064648W WO2008080993A3 WO 2008080993 A3 WO2008080993 A3 WO 2008080993A3 EP 2007064648 W EP2007064648 W EP 2007064648W WO 2008080993 A3 WO2008080993 A3 WO 2008080993A3
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- substituted
- adamantylarylmagnesium
- halides
- adamantylarylhalide
- preparing
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 4
- 150000004820 halides Chemical class 0.000 title abstract 3
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 abstract 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- 239000003153 chemical reaction reagent Substances 0.000 abstract 2
- 238000003786 synthesis reaction Methods 0.000 abstract 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 1
- 229910052786 argon Inorganic materials 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000012039 electrophile Substances 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
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
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/02—Magnesium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention concerns fine organic synthesis, particularly the method for preparing of substituted adamantylarylmagnesium halides. The known methods for preparing Grignard's reagent from substituted adamantylarylhalide give very low yeld of the desired product. Substituted adamantylarylhalides are active intermediates that by interacting with various electrophiles provide for a wide range of biologically active compounds. The aim of current invention was to develop a method for preparing substituted adamantylarylmagnesium halides. The aim was attained adding lithium chloride in the Grignard's reagent synthesis by acting on magnesium metal in dry tetrahydrofuran under argon by substituted adamantylarylhalide. It was demonstrated that adding lithium chloride to adamantylarylhalide within a range from 1:1 to 1:2 provides for stable high yield of the desired end product.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EA200900899A EA015949B1 (en) | 2006-12-28 | 2007-12-28 | A method for preparation of substituted adamantylarylmagnesium halides |
| US12/448,671 US20100113816A1 (en) | 2006-12-29 | 2007-12-28 | Method for prepartion of substituted adamantylarymagnesium halides |
| EP07858234A EP2129679A2 (en) | 2006-12-28 | 2007-12-28 | A method for preparation of substituted adamantylarylmagnesium halides |
| UAA200907979A UA97507C2 (en) | 2006-12-28 | 2007-12-28 | Method for preparing of substituted adamanty-larylmagnesium halides |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LV060151A LV13735B (en) | 2006-12-28 | 2006-12-28 | Method for manufacturing substituted adamantylarylmagnesium chalogenides |
| LVP-06-151 | 2006-12-29 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO2008080993A2 WO2008080993A2 (en) | 2008-07-10 |
| WO2008080993A3 true WO2008080993A3 (en) | 2009-03-12 |
Family
ID=39589040
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP2007/064648 WO2008080993A2 (en) | 2006-12-28 | 2007-12-28 | A method for preparation of substituted adamantylarylmagnesium halides |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP2129679A2 (en) |
| EA (1) | EA015949B1 (en) |
| LV (1) | LV13735B (en) |
| UA (1) | UA97507C2 (en) |
| WO (1) | WO2008080993A2 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113866292B (en) * | 2021-09-13 | 2024-03-19 | 河北威远生物化工有限公司 | Method for measuring content of o-chlorobenzyl magnesium chloride |
| CN117511212B (en) * | 2023-11-09 | 2024-04-12 | 东莞市好易达新材料科技有限公司 | High-temperature-resistant silicone glass fiber sleeve and preparation method thereof |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100348569C (en) | 2001-11-30 | 2007-11-14 | 伯哈姆学院 | Induction of apoptosis in cancer cells |
| EP1582523A1 (en) | 2004-04-02 | 2005-10-05 | Ludwig-Maximilians-Universität München | Method of preparing organomagnesium compounds |
-
2006
- 2006-12-28 LV LV060151A patent/LV13735B/en unknown
-
2007
- 2007-12-28 EA EA200900899A patent/EA015949B1/en not_active IP Right Cessation
- 2007-12-28 UA UAA200907979A patent/UA97507C2/en unknown
- 2007-12-28 WO PCT/EP2007/064648 patent/WO2008080993A2/en active Application Filing
- 2007-12-28 EP EP07858234A patent/EP2129679A2/en not_active Withdrawn
Non-Patent Citations (1)
| Title |
|---|
| LIU, ZHICHANG ET AL: "A high yield and pilot-scale process for the preparation of adapalene", ORGANIC PROCESS RESEARCH & DEVELOPMENT , 10(2), 285-288 CODEN: OPRDFK; ISSN: 1083-6160, 2006, XP002498088 * |
Also Published As
| Publication number | Publication date |
|---|---|
| UA97507C2 (en) | 2012-02-27 |
| LV13735B (en) | 2008-09-20 |
| EP2129679A2 (en) | 2009-12-09 |
| EA015949B1 (en) | 2011-12-30 |
| WO2008080993A2 (en) | 2008-07-10 |
| EA200900899A1 (en) | 2010-02-26 |
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