Processes for the preparation of 1,4-diaryl-2-fluoro-1,3-butadiene and 1,4-diaryl-2-fluoro 2 butene compounds

A process for the preparation of a 1,4-diaryl-2-fluoro-1,3-butadiene compound of the structural formula I

• wherein
• R is C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl or C3-C6-halocycloalkyl;
• Ar is phenyl optionally substituted with any combination of from one to three halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy groups,
• 1- or 2-naphthyl optionally substituted with any combination of from one to three halogen, C1-C4-alkyl, C1-C4haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy groups;
• and
• Ar1 is phenoxyphenyl optionally substituted with any combination of from one to six halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy groups,
• phenyl optionally substituted with any combination of from one to five halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, or C1-C4-haloalkoxy groups,
• biphenyl optionally substituted with any combination of from one to five halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy groups,
• benzylphenyl optionally substituted with any combination of from one to five halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy groups,
• benzoylphenyl optionally substituted with any combination of from one to five halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy groups, or
• 1- or 2-naphthyl optionally substituted with any combination of from one to three halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy groups,
• which process comprises reacting an arylmethanesulfonyl fluoride or arylmethanephosphonate compound of the structural formula II
• Ar1CH2Y (II)
• wherein Y is SO2F or P(O)(OR1)2, R1 is C1-C4-alkyl, and Ar1 is as described above with a 3-aryl-2-fluoropropenal compound of the structural formula III
• wherein R and Ar are as hereinbefore defined, in the presence of a base.