Potassium Carbonate → Azoxystrobin

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-cyanophenol (13.2 g), potassium carbonate (20.7 g), N-methyl-2-pyrrolidinone (15.0 g), (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxypropenoate (32.8 g) and water (35 g) was heated at 105° C. for 15 hours. Any distillates were allowed to come off under atmospheric conditions. The reaction mixture was mixed with toluene. The organic layer was then separated. Toluene and N-methyl-2-pyrrolidinone were removed from the organic phase by vacuum distillation (110° C., 20 mmHg). The melt was cooled to 90° C. after which methanol (40 ml) was added to help cooling to 65-75° C. The resulting mixture was cooled to ambient and kept at this temperature overnight. 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 (68.2% isolated yield).

Provenance & Evidence