Process for the preparation of 2-(pyrid-2-yloxymethyl) phenylacetates
AssigneeCorteva Agriscience LLC
InventorsJAMES J. HENKELIS, NICHOLAS M. IRVINE, MARK ONDARI, RAFAEL SHAPIRO, ERIC WIENSCH
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Abstract
Described herein are processes for the preparation of 2-(pyrid-2-yloxymethyl)-phenylacetates which are useful as intermediates for agricultural products. The processes comprise reacting a substituted pyridine with phenylacetic acid alcohol dianions derived from 3-isochromanone. The intermediates may be further reacted to form agricultural products such as fungicides.
Claims22
A process for preparing a compound of formula (II)
- wherein Z is halo, haloalkyl, haloalkoxy, phenyl, phenoxy, amino, alkylamino, dialkylamino, acylamino, cyano, carboxy, alkoxycarbonyl, or alkylcarbonyloxy;
- and Yn wherein n=0, 1, 2, or 3 is independently halo, haloalkyl, haloalkoxy, phenyl, phenoxy, amino, alkylamino, dialkylamino, acylamino, cyano, carboxy, alkoxycarbonyl, or alkylcarbonyloxy;
- and R is C1 to C4, branched or unbranched, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, or haloalkynyl which comprises:
- a) reacting a 2-fluoropyridine of formula (IV) in a solvent;
- with a compound of formula (III) wherein M is lithium, sodium, potassium, or any other metal suitable for making alkoxides and carboxylates;
- to obtain a compound of formula (V);
- and
- b) reacting the compound of formula (V) with a compound of formula R-L, wherein L is fluoro, chloro, bromo, iodo, sulfate, fluorosulfonate, alkylsulfonate, phenylsulfonate, substituted phenylsulfonate, or the equivalent, to obtain a compound of formula (II).
A process for preparing a compound of structure (I) wherein Z is halo, haloalkyl, haloalkoxy, phenyl, phenoxy, amino, alkylamino, dialkylamino, acylamino, cyano, carboxy, alkoxycarbonyl, or alkylcarbonyloxy;
- and wherein Yn is independently halo, haloalkyl, haloalkoxy, phenyl, phenoxy, amino, alkylamino, dialkylamino, acylamino, cyano, carboxy, alkoxycarbonyl, or alkylcarbonyloxy and n=0 to 3;
- and wherein R and R′ are the same or different and selected from C1 to C4, branched or unbranched, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, or haloalkynyl;
- which comprises:
- a) reacting a 2-fluoropyridine of formula (IV) in a solvent;
- with a compound of formula (III) wherein M is lithium, sodium, potassium, or any other metal suitable for making alkoxides and carboxylates;
- to obtain a compound of formula (V);
- and
- b) alkylating a compound of formula (V) with a compound of formula R-L, wherein L is fluoro, chloro, bromo, iodo, sulfate, fluorosulfonate, alkylsulfonate, phenylsulfonate, substituted phenylsulfonate or the equivalent;
- to obtain a compound of formula (II);
- and
- c) reacting a compound of formula (II) with an alkyl formate to form a mixture of compounds of formula (IX);
- and
- d) alkylating the mixture of compounds of formula (IX) with a compound of formula R′-L′ wherein and L′ is fluoro, chloro, bromo, iodo, sulfate, fluorosulfonate, alkylsulfonate, phenylsulfonate, substituted phenylsulfonate or the equivalent;
- to form a compound of formula (I).
Dependencies are inferred from the claim text.