Process for the preparation of substituted difluorobenzo-1,3-dio

Details Process for the preparation of substituted difluorobenzo-1,3-dio Process for the preparation of substituted difluorobenzo-1,3-dio

1995-05-12

1996-05-07

McKane, Joseph K.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549213, 549214, 549434, C07D31706

Patent

active

055148166

ABSTRACT:
The reaction of 2,2-difluorobenzo-1,3-dioxole with (a) an alkali metal or an alkali metal compound and then (b) a compound R.sup.1 -Z.sup.1 in which Z.sup.1 is a leaving group, or with an aldehyde produces compounds of formula I ##STR1## wherein R.sup.1 is --OH, --SH, --CHO, --CN, --COOH, --B(OH).sub.2, --COX, with X being C1 or Br, or is --COOR.sup.2, --SiR.sup.2.sub.3 or --B(OR.sup.2).sub.2, with R.sup.2 being a C.sub.1 -C.sub.12 alcohol moiety without the hydroxy group, wherein R.sup.1 is further --C.sub.n H.sub.2n COOR.sup.2, with n being an integer from 1 to 4, or linear or branched C.sub.1 -C.sub.12 hydroxyalkyl which is unsubstituted or is substituted by --F, --CN, C.sub.1 -C.sub.6 alkoxy, phenyl, fluorophenyl, C.sub.1 -C.sub.4 alkoxy-phenyl, C.sub.1 -C.sub.4 alkylthio-phenyl, C.sub.1 -C.sub.4 alkylphenyl, C.sub.1 -C.sub.4 fluoroalkyl-phenyl, nitrophenyl or by cyanophenyl, or wherein R.sup.1 is a benzyl alcohol which is unsubstituted or is substituted by F, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 fluoroalkyl, nitro or by cyano, or is C.sub.1 -C.sub.12 acyl, or wherein R.sup.1 is a radical of formula II ##STR2## wherein R.sup.5 is --CN, --CF.sub.3, --COOR.sup.2, --CONH.sup.2, --CO--NHR.sup.2 or --CONR.sup.2.sub.2, R.sup.3 and R.sup.4 are a direct bond or each is H, or R.sup.3 is H and R.sup.4 independently has the meanings of R.sup.5, or R.sup.3 and R.sup.4 together are --CH.sub.2 --NR.sup.6 --CH.sub.2 --, --CH.sub.2 --NR.sup.6 --CO-- or --CO--NR.sup.6 --CO-- wherein R.sup.6 is the radical of a removable protecting group, or wherein further R.sup.1 is a radical of formula III ##STR3## Insecticides or fungicides can be prepared from the compounds of formula I.

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