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

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

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549214, 549430, 549437, 549441, 549445, 549447, C07D31750, C07D31752, C07D31754

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054203015

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 Cl or Br, or is --COOR.sup.2, --SiR.sub.3.sup.2 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 alkyl-phenyl, 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.sub.2.sup.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.
3-(2,2-difluorobenzodioxol-4-yl)-4-cyanopyrrole can be prepared by reacting 4-metallo-2,2-difluorobenzodioxole (III) with an unsaturated nitrile and then with a sulfonylmethyl isocyanide in a one-pot process. The compounds III are novel intermediates.

REFERENCES:
patent: 4502882 (1985-03-01), Carter
patent: 4705800 (1987-11-01), Nyfeler et al.
patent: 4722935 (1988-02-01), Ehrenfreund
patent: 4780551 (1988-10-01), Nyfeler et al.
patent: 4886816 (1989-12-01), Franckowiak et al.
patent: 4912229 (1990-03-01), Wollweber
patent: 4923994 (1990-05-01), Wollweber
patent: 4925840 (1990-05-01), Nyfeler et al.
J. Org. Chem, vol. 37, No. 4, 1972, p. 673.
Synthesis Heterocyclic Compounds, pp. 957-986, 1983.
CA111:153617S Preparation, . . . microbicides. Ackermann, et al, p. 703, 1989.
CA114:101724s Preparation, . . . fungicides. Sutter, p. 721, 1991.
CA 107:176019e Manufacture of . . . fungicides. Kohl et al., p. 724, 1987.
CA 111:7416j Preparation of . . . regulators, Daum et al., p. 713, 1989.
CA111:77991s Preparation of . . . therefrom, Ehrenfreund, p. 753, 1989.
CA 118:6861h Process for . . . fungicides. Knueppel et al., p. 729, 1993.
Advanced Organic Chemistry, 2nd Ed., Mar. pp. 554-557, 566-569, 1977.
J. Org. Chemistry vol. 37, No. 4, Stogryn, A New Synthesis of 3,4-(Difluoromethylenedioxy)benzaldehyde, 1972, p. 673.

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