Preparation of fluorinated anilines

1. A process for preparing a compound(s) of the formula (I)

in which

m is an integer in the range from 0 to (5-n-p)

n is 1, 2, 3 or 4 and

p is 0, 1 or 2,

where the sum of

n+p is a maximum of 4 and

R 1 is in each case independently hydrogen, fluorine, C 1 –C 12 -alkyl, C 5 –C 14 -aryl, C 6 –C 15 -arylalkyl, C 1 –C 12 -fluoroalkyl, C 1 –C 12 -fluoroalkylthio, C 1 -C 12 -fluoroalkoxy, C 1 –C 12 -alkylsulphonyl or radicals of the formulae (IIa) to (IIf)

A-CN  (IIa)

A-CON(R 2 ) 2 —  (IIb)

A-CO 2 R 2   (IIc)

A-CONH 2   (IId)

A-COHal 2   (IIe)

A-B—R 2   (IIf)

where, in the formulae (IIa) to (IIf),

A is absent or is a C 1 –C 8 -alkylene or C 1 –C 8 -fluoroalkylene radical and

B is oxygen or NR 2 , and

R 2 is in each case independently C 1 -C 8 -alkyl, C 6 –C 15 -arylalkyl or C 5 –C 14 -aryl, or C 5 –C 14 -aryl, or N(R 2 ) 2 as a whole is optionally a cyclic amino radical having a total of 4 to 12 carbon atoms and

Hal 1 is chlorine or bromine,

comprising:

in a step A), converting

a compound(s) of the formula (III)

in which

R 1 , Hal 1 , m, p and n are each as defined above

in the presence of ionic fluoride to a compound(s) of the formula (IV)

and,

in a step B), converting

the compound(s) of the formula (IV) to the compound(s) of the formula (I) with a reducing agent.

2. The process according to claim 1 , wherein the compound(s) of the formula (I) are chosen from 2,4,6-trifluoroaniline, 2-trifluoromethyl-4-fluoroaniline, 4-trifluoromethyl-2-fluoroaniline, 4-trifluoromethyl-2,6-difluoroaniline and 3-trifluoromethyl-2,4,6-trifluoroaniline.

3. The process according to claim 1 , wherein the compound(s) of the formula (III) is prepared, in a first step, by halogenating a compound(s) of the formula (V) to give a compound(s) of the formula (VI), where, in the formulae (V) and (VI)

R 1 , Hal 1 , n, p and m are each as defined in claim 1 and, in a subsequent step, oxiziding the—compound(s) of the formula (VI) to the compound(s) of the formula (III).

4. The process according to claim 1 , wherein the ionic fluoride used is a quatemary ammonium fluoride, phosphonium fluoride, an alkali metal fluoride or a mixture thereof.

5. The process according to claim 1 , wherein step A) is carried out in the presence of a phase transfer catalyst(s) and/or a halex catalyst(s).

6. The process according to claim 1 , wherein step A) is carried out in the presence of an organic solvent(s).

7. The process according to claim 1 , wherein the reaction temperature in step A) is 120° C. to 250° C.

8. 2,2′-Dichloro4,4′-bistrifluoromethylazobenzene, 2,2′,6,6′-tetrachloro-4,4′-bistrifluoro-methylazobenzene, 2,2′,4,4′,6,6′-hexachloro-3,3′-bistrifluoromethylazobenzene and 4,4′-dichloro-2,2′-bistrifluoromethylazobenzene.

9. 2,2′-Difluoro-4,4′-bistrifluoromethylazobenzene, 2,2′,6,6′-tetrafluoro-4,4′-bistrifluoro-methylazobenzene, 2,2′,4,4′,6,6′-hexafluoro-3,3′-bistrifluoromethylazobenzene and 4,4′-difluoro-2,2′-bistrifluoromethylazobenzene.