Process for the preparation of 5-bromo-1,2,3-trichlorobenzene

Patent metadata

Field	Value
Publication number	US-9975823-B2
Application number	US-201515515322-A
Country	US
Kind code	B2
Filing date	Oct 8, 2015
Priority date	Oct 14, 2014
Publication date	May 22, 2018
Grant date	May 22, 2018

Abstract

The present invention relates to a process for the preparation of a compound of formula I (I), comprising reacting a compound of formula II (II), with a brominating agent in the presence of an acidic catalyst to a compound of formula III (III), and reacting the compound of formula III in tetrahydrofuran or 2-methyl-tetrahydrofuran with potassium tert-butoxide to a compound of formula I.

First claim

The invention claimed is:

1. A process for the preparation of a compound of formula I

comprising
a) reacting a compound of formula II

with a brominating agent in the presence of an acidic catalyst to a compound of formula III,

and, wherein the acidic catalyst is sulfuric acid, hydrochloric acid, phosphoric acid, Lewis acids or acidic catalyst prepared in situ by mixing bromine with iron powder; and wherein the brominating agent is bromine or N-bromo succinimide;
b) reacting the compound of formula III in tetrahydrofuran or 2-methyl-tetrahydrofuran with potassium tert-butoxide to form a compound of formula I.

2. A process according to claim 1 , wherein the Lewis acid is iron (III) bromide, aluminum bromide, boron trifluoride etherate or titanium tetrachloride.

3. A process according to claim 1 , wherein the compound of formula III is reacted in tetrahydrofuran with potassium tert-butoxide to form a compound of formula I.

4. A process according to claim 1 comprising
a) reacting a compound of formula II

with a brominating agent selected from the group consisting of bromine and N-bromo succinimide in the presence of an acidic catalyst selected from the group consisting of sulfuric acid, hydrochloric acid, phosphoric acid, Lewis acids and acidic catalyst prepared in situ by mixing bromine with iron powder, to form a compound of formula III,

and
b) reacting the compound of formula III in tetrahydrofuran with potassium tert-butoxide to form a compound of formula I.

Assignees

• Syngenta Participations Ag

Inventors

• Smits Helmars

Classifications

• C07C25/02

  Monocyclic aromatic halogenated hydrocarbons · CPC title

• C07C17/358 Primary

  by isomerisation · CPC title

• C07C17/06

  combined with replacement of hydrogen atoms by halogens · CPC title

• C07C17/04 Primary

  to unsaturated halogenated hydrocarbons · CPC title

• C07C17/12 Primary

  in the ring of aromatic compounds · CPC title