Process for producing 2,5-dihalophenolethers

Patent metadata

Field	Value
Publication number	US-9957212-B2
Application number	US-201515119654-A
Country	US
Kind code	B2
Filing date	Feb 19, 2015
Priority date	Feb 21, 2014
Publication date	May 1, 2018
Grant date	May 1, 2018

Abstract

The present invention relates to a process for providing a compound of formula (IV):

wherein R 1 and R 2 are each independently C 1 -C 4 alkyl, and Hal is independently Cl or Br, the process comprising the steps of: (i) reacting a compound of formula (II)

wherein R 1 and Hal is defined as above, to obtain a compound of formula (III)

wherein R 1 and Hal is defined as above, and (ii) reacting the compound of formula (III) to obtain the compound of formula (IV).

First claim

The invention claimed is:

1. A process of making a compound of formula (V)

wherein R 2 is C 1 -C 4 alkyl;

comprising the steps of:
(i) reacting a compound of formula (II)

in the presence of a chlorination agent to obtain a compound of formula (III)

(ii) reacting the compound of formula (III) to obtain the compound of formula (IV)

and
(iii) reacting the compound of formula (IV), wherein R 1 and R 2 are each independently C 1 -C 4 alkyl, in the presence of an oxidation agent to obtain the compound of formula (V).

2. The process according to claim 1 , wherein step (i) is carried out in the presence of a chlorinating agent selected from sulfurylchloride, N-chlorosuccinimide (NCS), N-chloroalkylamine, N-chlorodialkylamine, and N-dichloroalkylamine, optionally in the further presence of a secondary amine.

3. The process according to claim 1 , wherein step (ii) is carried out in the presence of a base and an alkylating agent selected from (R 2 ) 2 SO 4 , (R 2 O) 2 CO, R 2 I, R 2 Br, and R 2 Cl.

4. The process according to claim 1 , wherein the compound of formula (II) is obtained by reacting a compound of formula (I)

in the presence of an alkali metal hydroxide or alkali metal alkoxide.

5. The process according to claim 1 , wherein
(a) R 1 is methyl, and/or
(b) R 2 is methyl.

6. The process according to claim 1 , wherein the compound of formula (V) is

7. The process according to claim 1 , comprising the steps:
(i) reacting a compound of formula (I)

in the presence of an alkali metal hydroxide or alkali metal alkoxide to obtain a compound of formula (II)

(ii) reacting the compound of formula (II) to obtain a compound of formula (III)

(iii) reacting the compound of formula (III) to obtain a compound of formula (IV)

and
(iv) reacting the compound of formula (IV) to obtain a compound of formula (V)

wherein R 1 and R 2 are each independently C 1 -C 4 alkyl.

Assignees

• Basf Se

Inventors

• Klauber Eric George
• Rack Michael
• Zierke Thomas
• Holub Nicole
• Schmelebeck Gerald
• Ji Junmin
• CORTES David

Classifications

• C07C39/30

  the halogen being two chlorine atoms · CPC title

• C07C51/16

  by oxidation (C07C51/145 takes precedence) · CPC title

• C07C65/21

  containing ether groups, [IMAGE cpc-sch-C07C-0958.gif] groups,[IMAGE cpc-sch-C07C-0959.gif] groups, or[IMAGE cpc-sch-C07C-0960.gif] groups · CPC title

• C07C41/16 Primary

  by reaction of esters of mineral or organic acids with hydroxy or O-metal groups · CPC title

• C07C39/28

  the halogen being one chlorine atom · CPC title