GB1416181A - Processes for the manufacture of fluoroalkylaromatic compounds - Google Patents

Abstract

1416181 Fluoroalkyl aromatic compounds DEFENCE SECRETARY OF STATE FOR 17 Jan 1973 [17 Jan 1972] 2100/72 Heading C2C Fluorinated organic compounds having an aromatic group directly connected to a fluorinated alkyl group are prepared by treating an aromatic compound having an aromatic nucleus with a reactive halogeno-substituent, a fluorinated alkane having a chloro-substituent, and metallic copper in a dipolar aprotic solvent in the presence of a cuprometallation catalyst which is a bidentate or tridentate ligand capable of forming a complex with copper whereby the desired fluorinated organic compound is formed and separating out the desired compound. The term " reactive halogeno substituent " means bromine or iodine generally or chlorine when activated, e.g. when attached to a triazine ring or ortho to a nitro group in a benzene ring. The term "fluorinated alkane" means an alkane in which at least half the possible hydrogen sites are occupied by F atoms and other possible hydrogen sites may be occupied by substituents. When the fluorinated alkane group is difunctional, i.e. it contains two chloro substituents or one chloro and one bromo- or iodo-substituent a fluorinated organic compound is produced having a fluorinated alkylene group connected between two aromatic groups. The bidentate or tridentate ligand is preferably 2,2<SP>1</SP>-bipyridyl or 1,10-phenanthroline or a substituted derivative thereof, but it may also be, e.g. 2,2<SP>1</SP>-biquinolyl, di-(2-pyridyl)methane, 8-hydroxyquinoline, thiourea, rubeanic acid, 2,2<SP>1</SP>,2<SP>11</SP> - terpyridine or 1,1,1 - tris - (dimethylphosphino - methyl)ethane. In examples, (6H - dodecafluorohexyl)benzene, (8H - hexadecafluorooctyl)benzene, dimethyl 3 - (8H- hexadecafluorooctyl)phthalate and 1,3-diphenylhexafluoropropane are prepared.