Potassium Carbonate → Azoxystrobin

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-cyanophenol (41.0 g), potassium carbonate (62.1 g), potassium fluoride (12.3 g), tetrabutylammonium bromide (17.1 g), (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxypropenoate (98.9 g) and water (210 g) was heated at 90-95° C. for 22 hours. The reaction mixture was mixed with toluene and a further quantity of water. 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 85° C. after which methanol (120 ml) was added to help cooling to 70° C. The resulting mixture was cooled to 40° C. and kept at this temperature for 1 hour. 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)pheny]-3-methoxypropenoate as the residue (85.5% isolated yield).

Provenance & Evidence