Chlorine → 1-Chloro-4,5-difluoro-2-methylbenzene

As shown in the above reaction, a mixture of 4-chloro-1-methyl-4,5,5-trifluorocyclohexene (IIIa) and 5-chloro-1-methyl-4,4,5-trifluorocyclohexene (IIIb) is prepared by reacting chlorotrifluoroethylene (CTFE) (I) and isoprene (II) at temperature range of 390 to 480° C. through continuous vapor phase condensation in a flow reactor and distilling the resultant. The mixture is dehydrohalogenated in the presence of alkali metal hydroxide and a phase transition catalyst to form 3,4-difluorotoluene (IV). The 3,4-difluorotoluene is reacted with chlorine gas in the presence of catalysts consisting of ferro-shaving and ferric chloride at temperature range of -10 to 40° C. without using any organic solvent to form 2-chloro-4,5-difluorotoluene (V). The 2-chloro-4,5-difluorotoluene is photo-reacted with chlorine gas under a lighting mercury lamp at temperature range of 80 to 140° C. without using any organic solvent to form 2-chloro-4,5-difluorobenzotrichloride (VI). The 2-chloro-4,5-difluorobenzotrichloride is reacted with aqueous acid solution at temperature range of 35 to 80° C. without using any organic solvent to give 2-chloro-4,5-difluorobenzoic acid (VII). The 2-chloro-4,5-difluorobenzoyl chloride (VIII) according to the present invention is prepared by reacting 2-chloro-4,5-difluorobenzotrichloride (VI) with zinc oxide.

ORD record

ord-e55df5875a9c4f8089e4316376412196

Source dataset

uspto-grants-1999_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06008407