1,4-diaryl-2-fluoro-1-buten-3-ol compounds and their use in...

Details 1,4-diaryl-2-fluoro-1-buten-3-ol compounds and their use in... 1,4-diaryl-2-fluoro-1-buten-3-ol compounds and their use in...

2001-08-13

2002-01-29

Shippen, Michael L. (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Oxygen containing

C546S290000, C546S343000, C568S633000, C568S634000, C568S639000, C568S645000, C568S647000, C568S807000, C568S808000, C568S809000, C570S129000

Reexamination Certificate

active

06342642

ABSTRACT:

BACKGROUND OF THE INVENTION
1,4-Diaryl-2-fluoro-1,3-butadiene compounds, methods for their preparation, and their use as intermediates in the preparation of 1,4-diaryl-2-fluoro-2-butene insecticidal and acaricidal agents are described in EP 811593-A1. The methods described in EP 811593-A1 for the preparation of 1,4-diaryl-2-fluoro-1,3-butadiene compounds require the use of phosphonium halide compounds. However, these methods are not entirely satisfactory because the required phosphonium halide compounds are relatively expensive and produce undesirable by-products which are difficult to remove from the 1,4-diaryl-2-fluoro-1,3-butadiene compounds. Accordingly, a need exists in the art for an improved process for the preparation of 1,4-diaryl-2-fluoro-1,3-butadiene compounds which avoids the use of phosphonium halide compounds.
It is, therefore, an object of the present invention to provide new compounds which are useful in the preparation of 1,4-diaryl-2-fluoro-1,3-butadiene compounds.
It is also an object of the present invention to provide an improved process for the preparation of 1,4-diaryl-2-fluoro-1,3-butadiene compounds which avoids the use of phosphonium halide compounds.
It is a further object of this invention to provide an improved process for the preparation of 1,4-diaryl-2-fluoro-2-butene compounds.
Other objects and advantages of the present invention will be apparent to those skilled in the art from the description below and the appended claims.
SUMMARY OF THE INVENTION
The present invention provides 1,4-diaryl-2-fluoro-1-buten-3-ol compounds of the structural formula I
wherein
R is hydrogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
3
-C
6
cycloalkyl or C
3
-C
6
halocycloalkyl;
Ar is phenyl optionally substituted with any combination of from one to three halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups,
1- or 2-naphthyl optionally substituted with any combination of from one to three halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups, or
a 5- or 6-membered heteroaromatic ring optionally substituted with any combination of from one to three halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups; and
Ar
1
is phenoxyphenyl optionally substituted with any combination of from one to six halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups,
phenyl optionally substituted with any combination of from one to five halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups,
biphenyl optionally substituted with any combination of from one to five halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups,
phenoxypyridyl optionally substituted with any combination of from one to five halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups,
benzylpyridyl optionally substituted with any combination of from one to five halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups,
benzylphenyl optionally substituted with any combination of from one to five halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups,
benzoylphenyl optionally substituted with any combination of from one to five halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups,
1- or 2-naphthyl optionally substituted with any combination of from one to three halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups, or
a 5- or 6-membered heteroaromatic ring optionally substituted with any combination of from one to three halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups.
The present invention also provides a new process for the preparation of 1,4-diaryl-2-fluoro-1,3-butadiene compounds of the structural formula II
wherein
R is hydrogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
3
-C
6
cycloalkyl or C
3
-C
6
halocycloalkyl;
Ar is phenyl optionally substituted with any combination of from one to three halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups,
1- or 2-naphthyl optionally substituted with any combination of from one to three halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups, or
a 5- or 6-membered heteroaromatic ring optionally substituted with any combination of from one to three halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups; and
Ar
1
is phenoxyphenyl optionally substituted with any combination of from one to six halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups,
phenyl optionally substituted with any combination of from one to five halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups,
biphenyl optionally substituted with any combination of from one to five halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups,
phenoxypyridyl optionally substituted with any combination of from one to five halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups,
benzylpyridyl optionally substituted with any combination of from one to five halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups,
benzylphenyl optionally substituted with any combination of from one to five halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups,
benzoylphenyl optionally substituted with any combination of from one to five halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups,
1- or 2-naphthyl optionally substituted with any combination of from one to three halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups, or
a 5- or 6-membered heteroaromatic ring optionally substituted with any combination of from one to three halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups, which process comprises reacting a 1,4-diaryl-2-fluoro-1-buten-3-ol compound of the structural formula I
wherein Ar, Ar
1
and R are as hereinbefore defined with a sulfonyl chloride or sulfonic acid anhydride compound and a base.
The present invention further provides a new process for the preparation of 1,4-diaryl-2-fluoro-2-butene compounds having the structural formula III
wherein
R is hydrogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
3
-C
6
cycloalkyl or C
3
-C
6
halocycloalkyl;
Ar is phenyl optionally substituted with any combination of from one to three halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups,
1- or 2-naphthyl optionally substituted with any combination of from one to three halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups, or
a 5- or 6-membered heteroaromatic ring optionally substituted with any combination of from one to three halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups; and
Ar
1
is phenoxyphenyl optionally substituted with any combination of from one to six halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups,
phenyl optionally substituted with any combination of from one to five halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups,
biphenyl optionally substituted with any combination of from one to five halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups,
phenoxypyridyl optionally substituted with any combination of from one to five halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups,
benzylpyridyl optionally substituted with any combination of from one to five halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups,
benzylphenyl optionally substituted with any combination of from on

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