Diorganomagnesium compound

Patent metadata

Field	Value
Publication number	US-12565507-B2
Application number	US-202017785952-A
Country	US
Kind code	B2
Filing date	Dec 14, 2020
Priority date	Dec 17, 2019
Publication date	Mar 3, 2026
Grant date	Mar 3, 2026

Abstract

A diorganomagnesium compound of formula R B —Mg—R A is provided. R B is different from R A , R B comprises a benzene nucleus substituted with a magnesium atom, one of the carbon atoms of the benzene nucleus ortho to the magnesium is substituted with a methyl, an ethyl, an isopropyl or forming a ring with the carbon atom which is its closest neighbour and which is meta to the magnesium. The other carbon atom of the benzene nucleus ortho to the magnesium is substituted with a methyl, an ethyl or an isopropyl. R A is an alkyl, a cycloalkyl or a benzyl, which may be substituted or unsubstituted, which diorganomagnesium compound is other than n-butylmesitylmagnesium. When used as co-catalyst of a metallocene, it makes it possible to increase the functional group content in the synthesis of a functional polymer.

First claim

The invention claimed is:

1 . An asymmetric diorganomagnesium compound of formula (I)
R B —Mg—R A   (I),
R B being different from R A , R B comprising a benzene ring substituted with the magnesium atom, one of the carbon atoms of the benzene ring ortho to the magnesium atom being substituted with a methyl, an ethyl, an isopropyl or forming a ring with the carbon atom which is its closest neighbor and which is meta to the magnesium atom, the other carbon atom of the benzene ring ortho to the magnesium atom being substituted with a methyl, an ethyl or an isopropyl, R A being an alkyl, a cycloalkyl or a benzyl, which may be substituted or unsubstituted, wherein the diorganomagnesium compound is other than n-butylmesitylmagnesium.

2 . The asymmetric diorganomagnesium compound according to claim 1 , in which R A represents an alkyl containing from 2 to 10 carbon atoms.

3 . The asymmetric diorganomagnesium compound according to claim 1 , in which R A represents a linear alkyl.

4 . A process for preparing an asymmetric diorganomagnesium compound of formula R B —Mg—R A , which comprises the placing in contact of an organometallic compound of formula R A M with an organomagnesium agent of formula R B —Mg—X and the reaction of the organometallic compound of formula R A M and of the organomagnesium agent of formula R B —Mg—X,
M representing a lithium, sodium or potassium atom,
X representing a leaving group,
R B being different from R A ,
R B comprising a benzene ring substituted with the magnesium atom, one of the carbon atoms of the benzene ring ortho to the magnesium atom being substituted with a methyl, an ethyl, an isopropyl or forming a ring with the carbon atom which is its closest neighbor and which is meta to the magnesium atom, the other carbon atom of the benzene ring ortho to the magnesium atom being substituted with a methyl, an ethyl or an isopropyl,
R A being an alkyl, a cycloalkyl or a benzyl, which may be substituted or unsubstituted, said diorganomagnesium compound being other than n-butylmesitylmagnesium.

5 . The process according to claim 4 , in which X is a halogen atom.

6 . The process according to claim 4 , in which X is a bromine atom or a chlorine atom.

7 . The process according to claim 4 , in which M represents a lithium atom.

8 . The asymmetric diorganomagnesium compound according to claim 1 , in which the carbon atoms of the benzene ring of R B ortho to the magnesium atom are substituted with a methyl.

9 . The asymmetric diorganomagnesium compound according to claim 2 , in which R A represents an alkyl containing from 2 to 8 carbon atoms.

10 . The process according to claim 6 , in which X is a bromine atom.

11 . The process according to claim 4 , in which, if one of the two carbon atoms of the benzene ring of R B ortho to the magnesium atom is substituted with an isopropyl, the second carbon atom of the benzene ring of R B ortho to the magnesium atom is not substituted with an isopropyl.

12 . The process according to claim 4 , in which the carbon atoms of the benzene ring of R B ortho to the magnesium atom are substituted with a methyl or an ethyl.

13 . A process for preparing an asymmetric diorganomagnesium compound of formula (II)

in which R 1 and R 5 represent a methyl or an ethyl,
R 2 , R 3 and R 4 , which may be identical or different, represent a hydrogen atom or an alkyl,
R A is an alkyl, a cycloalkyl or a benzyl, which may be substituted or unsubstituted,
which comprises the placing in contact of an organometallic compound of formula R A M with an organomagnesium agent of formula R B —Mg—X and the reaction of the organometallic compound of formula R A M and of the organomagnesium agent of formula R B —Mg—X,
the organomagnesium agent of formula R B —Mg—X being of the formula:

M representing a lithium, sodium or potassium atom, and
X representing a leaving group,
said diorganomagnesium compound of formula (II) being other than n-butylmesitylmagnesium.

14 . An asymmetric diorganomagnesium compound of formula (II)

in which
R 1 and R 5 represent a methyl or an ethyl,
R 2 , R 3 and R 4 , which may be identical or different, represent a hydrogen atom or an alkyl,
R A is an alkyl, a cycloalkyl or a benzyl, which may be substituted or unsubstituted said diorganomagnesium compound of formula (II) being other than n-butylmesitylmagnesium.

15 . The asymmetric diorganomagnesium compound according to claim 14 , in which R 1 , R 3 and R 5 are identical.

16 . The asymmetric diorganomagnesium compound according to claim 14 , in which R 2 and R 4 represent a hydrogen atom.

17 . The asymmetric diorganomagnesium compound according to claim 14 , in which R A represents an alkyl containing from 2 to 10 carbon atoms.

18 . The asymmetric diorganomagnesium compound according to claim 17 , in which R A represents an alkyl containing from 2 to 8 carbon atoms.

19 . The asymmetric diorganomagnesium compound according to claim 14 , in which R A represents a linear alkyl.

20 . The asymmetric diorganomagnesium compound according to claim 14 , in which R 1 and R 5 represent a methyl.

Assignees

• Michelin & Cie

Inventors

• Thuilliez Julien
• Ngo Robert
• Jean-Baptiste-Dit-Dominique François

Classifications

• C08F210/02 Primary

  Ethene · CPC title

• C07F3/02 Primary

  Magnesium compounds · CPC title