US 9,809,543 B2
Method for producing 2,3-dichloro-5-(trichloromethyl)pyridine
Casper Stoubaek Andersen, Lemvig (DK)
Assigned to CHEMINOVA A/S, Harboøre (DK)
Appl. No. 14/898,416
Filed by CHEMINOVA A/S, Harboøre (DK)
PCT Filed Jun. 13, 2014, PCT No. PCT/DK2014/050166
§ 371(c)(1), (2) Date Dec. 14, 2015,
PCT Pub. No. WO2014/198278, PCT Pub. Date Dec. 18, 2014.
Claims priority of application No. 2013 70319 (DK), filed on Jun. 14, 2013; and application No. 2014 70138 (DK), filed on Mar. 20, 2014.
Prior Publication US 2016/0145211 A1, May 26, 2016
Int. Cl. C07D 213/61 (2006.01); C07D 213/643 (2006.01); C07D 213/74 (2006.01)
CPC C07D 213/61 (2013.01) [C07D 213/643 (2013.01); C07D 213/74 (2013.01)] 32 Claims
1. A method for preparing 2,3-dichloro-5-(trichloromethyl)pyridine of formula [II] by a process which comprises the steps:
(1) preparing a reaction mixture comprising a compound of the general formula [I] and PCl5,

OG Complex Work Unit Drawing
(i) X is COOH, CONH2, CCl3, or CN;
(ii) R1 represents H or Cl;
(iii) PCl5 acts as a chlorinating agent; and
(2) reacting said mixture at a pressure above 1 bar and a temperature above 70° C. and below 350° C.;
wherein, when R1 is H, an intermediate compound (A), 2-chloro-5-(trichloromethyl)pyridine, is formed; or
when R1 is H and X is COOH, an intermediate (B), 3-chloroformylpyridine, is formed; or
when R1 is Cl and X is COOH, an intermediate (B), 3-chloroformyl-5-chloropyridine, is formed in the process.