Process and intermediate compounds for the preparation of...

Details Process and intermediate compounds for the preparation of... Process and intermediate compounds for the preparation of...

1998-12-21

2001-07-17

Fan, Jane (Department: 1612)

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

Organic compounds

Halogen containing

Reexamination Certificate

active

06262319

ABSTRACT:

BACKGROUND OF THE INVENTION
Fluoroolefin compounds which are useful as pesticidal agents are described in WO 94/06741 and GB 2,288,803-A. Those references also describe processes for the preparation of fluoroolefin compounds. However, those processes are not entirely satisfactory because the fluoroolefin compounds are produced in relatively low yields. Those references also fail to teach how to make the intermediate compounds of the present invention.
SUMMARY OF THE INVENTION
The present invention provides an effective and efficient process for the preparation of a pesticidal fluoroolefin compound having the structural formula I
wherein
R is hydrogen or C
1
-C
4
alkyl, and
R
1
is C
1
-C
4
alkyl or cyclopropyl, or R and R
1
, are taken together with the carbon atom to which they are attached to form a cyclopropyl group;
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, or
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;
Ar
1
is phenoxyphenyl 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,
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, or
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; and
the configuration of the groups ArCRR
1
- and -CH
2
Ar
1
about
the double bond is predominately mutually trans, which process comprises reacting a 4-aryl-2-fluoro-2-butene-1-ol compound having the structural formula II
wherein Ar, R and R
1
are as described above, with a brominating agent to form a 4-aryl-1-bromo-2-fluoro-2-butene compound having the structural formula III
wherein Ar, R and R
1
are as described above, and reacting the formula III compound with a palladium catalyst, a base, and a boronic acid having the structural formula IV, a boronic anhydride having the structural formula V or a borate ester having the structural formula VI
(HO)
2
B—Ar
1
  (IV)
 (R
2
O)
2
B—Ar
1
  (VI)
wherein R
2
is C
1
-C
4
alkyl and Ar
1
is as described above.
The present invention also relates to the intermediate 4-aryl-1-bromo-2-fluoro-2-butene compounds of formula III.
It is, therefore, an object of the present invention to provide an effective and efficient process for the preparation of pesticidal fluoroolefin compounds.
It is also an object of the present invention to provide intermediate compounds which are useful for the preparation of pesticidal fluoroolefin 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.


REFERENCES:
patent: 5248834 (1993-09-01), Elliott et al.
patent: 5489592 (1996-02-01), Collonges et al.
patent: 5763700 (1998-06-01), Khambay et al.
patent: 5849958 (1998-12-01), Barnes et al.
patent: 5880162 (1999-03-01), Khambay et al.
patent: 2288803 (1995-01-01), None
patent: WO 94/06741 (1994-03-01), None
Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, Mar. 1968 by McGraw-Hill.

Affiliated with

Also associated with

Rating

Process and intermediate compounds for the preparation of... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Process and intermediate compounds for the preparation of..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process and intermediate compounds for the preparation of... will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2543877