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US 6,903,239 B2Granted
Fluorinated benzaldehydes
AssigneeBayer Chemical Aktiengesellschaft
InventorsKaren Peilstöcker, Albrecht Marhold
Life of this patent
Estimating the term…
Abstract
The present invention relates to fluorinated benzaldehydes, to a process for preparing them and also to the use of the fluorinated benzaldehydes for preparing active ingredients, especially in medicaments and agrochemicals.
Claims21
A process for preparing compounds of the formula (I)
- where
- R1 is in each case independently C1-C12-alkyl, chlorine or bromine or a radical of the formulae (IIa) or (IIb)
- A-B-D-E (IIa)
- A-E (IIb)
- where, each independently,
- A is absent or is a C1-C8-alkylene radical and
- B is absent or is oxygen, sulphur or NR2
- where R2 is hydrogen or C1-C8-alkyl and
- D is a carbonyl group and
- E is C1-C8-alkyl, C1-C8-alkoxy, NH(C1-C8-alkyl) or N(C1-C8-alkyl)2 or is a cyclic amino radical having 4 to 12 carbon atoms and
- n is an integer of 0 to 3-m and
- RF is fluorine, C1-C12-fluoroalkyl, —O(C1-C12-fluoroalkyl) or —S(C1-C12-fluoroalkyl) and
- m is an integer of 1 to 3,
- comprising
- converting a compound of the formula (II)
- where R1 and RF, and also n and m, are as defined above
- in the presence of urotropin and
- in the presence of acid
- to compounds of the formula (I).
16 more elements
A compound of the formula (I)
- where
- R1 is in each case independently C1-C12-alkyl, chlorine or bromine or a radical of the formulae (IIa) or (IIb)
- A-B-D-E (IIa)
- A-E (IIb)
- where, each independently,
- A is absent or is a C1-C8-alkylene radical and
- B is absent or is oxygen, sulphur or NR2
- where R2 is hydrogen or C1-C8-alkyl and
- D is a carbonyl group and
- E is C1-C8-alkyl, C1-C8-alkoxy, NH(C1-C8-alkyl) or N(C1-C8-alkyl)2 or is a cyclic amino radical having 4 to 12 carbon atoms and
- n is an integer of 0 to 3-m and
- RF is fluorine, C1-C12-fluoroalkyl, —O(C1-C12-fluoroalkyl) or —S(C1-C12-fluoroalkyl) and
- m is an integer of 1 to 3.
10 more elements
A compound of the formula (II)
- where
- R1 is in each case independently C1-C12-alkyl, chlorine or bromine or a radical of the formulae (IIa) or (IIb)
- A-B-D-E (IIa)
- A-E (IIb)
- where, each independently,
- A is absent or is a C1-C8-alkylene radical and
- B is absent or is oxygen, sulphur or NR2
- where R2 is hydrogen or C1-C8-alkyl and
- D is a carbonyl group and
- E is C1-C8-alkyl, C1-C8-alkoxy, NH(C1-C8-alkyl) or N(C1-C8-alkyl)2 or is a cyclic amino radical having 4 to 12 carbon atoms and
- n is an integer of 0 to 3-m and
- RF is fluorine, C1-C12-fluoroalkyl, —O(C1-C12-fluoroalkyl) or —S(C1-C12-fluoroalkyl) and
- m is an integer of 1 to 3,
- with the exception of 4-fluoro-2-methylphenol.
11 more elements
A compounds of the formula (V)
- where
- R1 is in each case independently C1-C12-alkyl, chlorine or bromine or a radical of the formulae (IIa) or (IIb)
- A-B-D-E (IIa)
- A-E (IIb)
- where, each independently,
- A is absent or is a C1-C8-alkylene radical and
- B is absent or is oxygen, sulphur or NR2 where R2 is hydrogen or C1-C8-alkyl and
- D is a carbonyl group and
- E is C1-C8-alkyl, C1-C8-alkoxy, NH(C1-C8-alkyl) or N(C1-C8-alkyl)2 or is a cyclic amino radical having 4 to 12 carbon atoms and
- n is an integer of 0 to 3-m and
- RF is fluorine, C1-C12-fluoroalkyl, —O(C1-C12-fluoroalkyl) or —S(C1-C12-fluoroalkyl) and
- m is an integer of 1 to 3 and
- R3 and R4 are each independently C1-C8-alkyl or NR3R4 as a whole is a cyclic amino radical having a total of 4 to 12 carbon atoms,
- with the exception of 5-fluoro-2-hydroxy-N,N-dimethylbenzylamine.
11 more elements
Dependencies are inferred from the claim text.