Process for preparing 3-chloro-2-vinylphenol

Patent metadata

Field	Value
Publication number	US-10160707-B2
Application number	US-201515317912-A
Country	US
Kind code	B2
Filing date	Jun 8, 2015
Priority date	Jun 11, 2014
Publication date	Dec 25, 2018
Grant date	Dec 25, 2018

Abstract

The present invention describes a novel process for preparing 3-chloro-2-vinylphenol which, owing to the chemoselectivity achieved, also allows direct conversion into (3-chloro-2-vinylphenyl)methane-sulphonate.

First claim

The invention claimed is:

1. A process for preparing a compound of formula (I),

comprising reacting a compound of formula (II),

with a base selected from the group consisting of lithium carbonate, sodium carbonate, potassium carbonate, calcium carbonate, triethylamine, diethylisopropylamine, tri-n-butylamine, pyridine, picoline, lutidine, and collidine; and
N,N-dimethylacetamide as a dipolar aprotic additive; and
optionally in the presence of a solvent selected from the group consisting of methyl tert-butyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, cyclopentyl methyl ether, 1,4-dioxane, ethyl acetate, n-propyl acetate, i-propyl acetate, and n-butyl acetate,
to give the compound of formula (I).

2. The process according to claim 1 , wherein the base is triethylamine, tri-n-butylamine, calcium carbonate, or lithium carbonate.

3. The process according to claim 1 , wherein the base is lithium carbonate.

4. The process according to claim 1 , wherein a solvent is used.

5. The process according to claim 4 , wherein the solvent is n-butyl acetate.

6. The process according to claim 4 , wherein the compound of formula (I) is not isolated but instead is directly converted further into a compound of formula (III)

wherein A is selected from the group consisting of mesyl, tosyl, acyl, phosphonyl, and phosphoryl;

using a base and a reagent Q-A, wherein Q is selected from the group consisting of chloride and bromide.

7. The process according to claim 6 , wherein Q is chloride and A is mesyl.

Assignees

• Bayer Cropscience Ag

Inventors

• Erver Florian
• Ford Mark James

Classifications

• C07C37/06 Primary

  by conversion of non-aromatic six-membered rings or of such rings formed in situ into aromatic six-membered rings, e.g. by dehydrogenation · CPC title

• C07C309/66 Primary

  Methanesulfonates · CPC title

• C07C39/373

  with all hydroxy groups on non-condensed rings and with unsaturation outside the aromatic rings · CPC title

• C07C303/28

  by reaction of hydroxy compounds with sulfonic acids or derivatives thereof · CPC title

• A01N31/08

  Oxygen or sulfur directly attached to an aromatic ring system · CPC title