Provided is a process for making 2-chloro-1,1,1,2-tetrafluoropropane. The process has the step of hydrofluorinating 2-chloro-3,3,3-trifluoropropene in the presence of a catalyst selected from the group consisting of SbCl.sub.3, SbCl.sub.5, SbF.sub.5, TiCl.sub.4, SnCl.sub.4, Cr.sub.2O.sub.3, and fluorinated Cr.sub.2O.sub.3.

The present invention provides a process for preparing a diester compound of the following general formula (1), having a dimethylcyclobutane ring, wherein R.sup.1 and R.sup.2 represent, independently of each other, a monovalent hydrocarbon group having 1 to 10 carbon atoms, the process comprising reacting a dimethylcyclobutanone compound of the following general formula (2), wherein R.sup.1 is as defined above, with a phosphonic ester compound of the following general formula (3), wherein R.sup.2 and R.sup.3 represent, independently of each other, a monovalent hydrocarbon group having 1 to 10 carbon atoms, to produce the diester compound (1), having a dimethylcyclobutane ring.

##STR00001##

The present invention provides a process for preparing a diester compound of the following general formula (1), having a dimethylcyclobutane ring, wherein R.sup.1 and R.sup.2 represent, independently of each other, a monovalent hydrocarbon group having 1 to 10 carbon atoms, the process comprising reacting a dimethylcyclobutanone compound of the following general formula (2), wherein R.sup.1 is as defined above, with a phosphonic ester compound of the following general formula (3), wherein R.sup.2 and R.sup.3 represent, independently of each other, a monovalent hydrocarbon group having 1 to 10 carbon atoms, to produce the diester compound (1), having a dimethylcyclobutane ring.

##STR00001##

Disclosed are 7,7′-dihalo-3,3,3′,3′-tetramethyl-1,1′-spirobiindane and a preparation method thereof. The 7,7′-dihalo-3,3,3′,3′-tetramethyl-1,1′-spirobiindane is a compound represented by formula I, or an enantiomer, a raceme or a diastereomer thereof. The compound of formula I could be prepared by using a racemic or optically active 3,3,3′,3′-tetramethyl-1,1′-spirobiindane-6,6′-diol as a raw material through a series of reactions. The 7,7′-dihalo-3,3,3′,3′-tetramethyl-1,1′-spirobiindane is a key intermediate for preparing 3,3,3′,3′-tetramethyl-1,1′-spirobiindane-based phosphine ligand compounds represented by formula II or III.

##STR00001##

Disclosed are 7,7′-dihalo-3,3,3′,3′-tetramethyl-1,1′-spirobiindane and a preparation method thereof. The 7,7′-dihalo-3,3,3′,3′-tetramethyl-1,1′-spirobiindane is a compound represented by formula I, or an enantiomer, a raceme or a diastereomer thereof. The compound of formula I could be prepared by using a racemic or optically active 3,3,3′,3′-tetramethyl-1,1′-spirobiindane-6,6′-diol as a raw material through a series of reactions. The 7,7′-dihalo-3,3,3′,3′-tetramethyl-1,1′-spirobiindane is a key intermediate for preparing 3,3,3′,3′-tetramethyl-1,1′-spirobiindane-based phosphine ligand compounds represented by formula II or III.

##STR00001##

A method for synthesizing 2-(1-cyclohexenyl)ethylamine. Cyclohexanone (II) is reacted with a Grignard reagent in a first organic solvent to produce 1-vinylcyclohexanol (III), which is then subjected to chlorination and rearrangement reaction with a chlorinating reagent in a second organic solvent in the presence of an organic base to synthesize (2-chloroethylmethylene)cyclolxane (IV). Then (2-chloroethylmethylene)cyclohexane (IV) and urotropine are subjected to quaternization in a third organic solvent to synthesize N-cyclohexylidene ethyl urotropine hydrochloride (V). Finally, the N-cyclohexylidene ethyl urotropine hydrochloride (V) undergoes hydrolysis and rearrangement reaction in a solvent in the presence of an inorganic mineral acid to synthesize 2-(1-cyclohexenyl)ethylamine (I).

A method for synthesizing 2-(1-cyclohexenyl)ethylamine. Cyclohexanone (II) is reacted with a Grignard reagent in a first organic solvent to produce 1-vinylcyclohexanol (III), which is then subjected to chlorination and rearrangement reaction with a chlorinating reagent in a second organic solvent in the presence of an organic base to synthesize (2-chloroethylmethylene)cyclolxane (IV). Then (2-chloroethylmethylene)cyclohexane (IV) and urotropine are subjected to quaternization in a third organic solvent to synthesize N-cyclohexylidene ethyl urotropine hydrochloride (V). Finally, the N-cyclohexylidene ethyl urotropine hydrochloride (V) undergoes hydrolysis and rearrangement reaction in a solvent in the presence of an inorganic mineral acid to synthesize 2-(1-cyclohexenyl)ethylamine (I).

A process for preparing a polyfluorinated compound of formula Ar—R.sub.1 (I), wherein Ar—R.sub.1 (I) is an aromatic ring system

##STR00001##

wherein R.sub.1 is selected from the group consisting of SF.sub.4Cl, SF.sub.3, SF.sub.2CF.sub.3, TeF.sub.5, TeF.sub.4CF.sub.3, SeF.sub.3, IF.sub.2, SeF.sub.2CF.sub.3, and IF.sub.4, X.sub.2 is N or CR.sub.2, X.sub.3 is N or CR.sub.3, X.sub.4 is N or CR.sub.4, X.sub.5 is N or CR.sub.5, X.sub.6 is N or CR.sub.6, and the total number of nitrogen atoms in the aromatic ring system is between 0 and 3, wherein R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are independently selected from the group consisting of hydrogen, fluoro, chloro, bromo, nitro, trifluoromethyl, 2,2,2-trifluoroethyl, pentafluorosulfanyl, phthalimido, azido, benzyloxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, methoxycarbonyl, ethoxycarbonyl, methylcarbonyl, ethylcarbonyl, acetoxy, t-butyl, phenylcarbonyl, benzylcarbonyl, 3-trifluoromethylphenyl, phenylsulfonyl, methylsulfonyl, chlorophenyl, methyldoxolonyl, methyl, isopropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, fluoromethyl, fluoroethyl and phenyl.

Provided is a process for making 2-chloro-1,1,1,2-tetrafluoropropane. The process has the step of hydrofluorinating 2-chloro-3,3,3-trifluoropropene in the presence of a catalyst selected from the group consisting of SbCl.sub.3, SbCl.sub.5, SbF.sub.5, TiCl.sub.4, SnCl.sub.4, Cr.sub.2O.sub.3, and fluorinated Cr.sub.2O.sub.3.

Provided is a process for making 2-chloro-1,1,1,2-tetrafluoropropane. The process has the step of hydrofluorinating 2-chloro-3,3,3-trifluoropropene in the presence of a catalyst selected from the group consisting of SbCl.sub.3, SbCl.sub.5, SbF.sub.5, TiCl.sub.4, SnCl.sub.4, Cr.sub.2O.sub.3, and fluorinated Cr.sub.2O.sub.3.