US 7,514,584 B2
Process for the production of 2(2-aminophenyl)-bicylopropane derivatives
Harald Walter, Basel (Switzerland); Camilla Corsi, Basel (Switzerland); Josef Ehrenfreund, Basel (Switzerland); Clemens Lamberth, Basel (Switzerland); Hermann Schneider, Basel (Switzerland); and Hans Tobler, Basel (Switzerland)
Assigned to Syngenta Crop Protection, Inc., Greensboro, N.C. (US)
Appl. No. 11/815,895
PCT Filed Feb. 20, 2006, PCT No. PCT/EP2006/001508
§ 371(c)(1), (2), (4) Date Aug. 09, 2007,
PCT Pub. No. WO2006/087223, PCT Pub. Date Aug. 24, 2006.
Claims priority of application No. 0302/05 (CH), filed on Feb. 21, 2005.
Prior Publication US 2008/0161610 A1, Jul. 03, 2008
Int. Cl. C07C 211/00 (2006.01); C07C 205/00 (2006.01)
U.S. Cl. 564—307  [568/928] 3 Claims
 
1. A process for the preparation of a compound of formula I

OG Complex Work Unit Drawing
wherein R1, R2 and R3 are each independently of the others hydrogen or methyl, which comprises
a) reaction of a compound of formula II

OG Complex Work Unit Drawing
wherein R1, R2 and R3 are as defined for formula I, either
a1) with triphenylphosphine dibromide or triphenylphosphine dichloride or
a2) with RSO2Cl, wherein R is C1-C4alkyl, C1-C4fluoroalkyl, benzyl, phenyl, nitrophenyl, halophenyl or C1-C6alkylphenyl, in the presence of a base,
to form a compound of formula III

OG Complex Work Unit Drawing
wherein X is OSO2R, wherein R is C1-C4alkyl, C1-C4fluoroalkyl, benzyl, phenyl, nitrophenyl, halophenyl or C1-C6alkylphenyl, or is bromine or chlorine and R1, R2 and R3 are as defined for formula I; and
b) reaction of that compound in the presence of a base to form a compound of formula IV

OG Complex Work Unit Drawing
wherein R1, R2 and R3 are as defined for formula 1; and
c) conversion of that compound in the presence of a reducing agent into a compound of formula I.