Potassium Carbonate → Azoxystrobin

Participants

Reaction Conditions

Reaction Steps

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxypropenoate in N,N-dimethylformamide (256.8 g, 33.69% strength) was vacuum distilled to remove the solvent. A solution of the potassium salt of 2-cyanophenol was then prepared by mixing 2-cyanophenol (37.0 g) and potassium carbonate (56.7 g) in water (209 g). This solution was added to the (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxypropenoate melt, which had previously been cooled to 80° C. Potassium fluoride (11.1 g) and tetrabutylammonium bromide (16.1 g) was then added to the reaction solution. The resulting mixture was stirred at 100° C. for 23 hours. Any distillates were allowed to come off under atmospheric conditions. Toluene and a further quantity of water was added to the solution. The organic layer was then separated. Toluene was removed from the organic phase by vacuum distillation (100° C., 20 mmHg). The melt was cooled to 90° C. after which methanol (108 ml) was added to help cooling to 65-75° C. The resulting mixture was cooled to 40° C. and kept at this temperature for 2 hours. It was then further cooled to 0-5° C. and held for another 1 hour period. The mixture was filtered to leave (E)-methyl 2-[2-(6-(2-cyanophenoxy)pyrimidin-4-yloxy)phenyl]-3-methoxypropenoate as the residue (67.0% isolated yield).

Provenance & Evidence