Potassium Carbonate → Azoxystrobin

Participants

Reaction Conditions

Reaction Steps

Methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropanoate in methylcyclohexane/chloromethoxypyrimidine (185.5 g, 59.71% strength) was vacuum distilled to leave the propanoate melt. A solution of the potassium salt of 2-cyanophenol was then prepared by mixing 2-cyanophenol (49.0 g) and potassium carbonate (30.4 g) in water (50 g). This solution was added to the methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropanoate melt, which had previously been cooled to 70° C. The reaction solution was then heated to 120° C. and held for 2 hours. Any distillates were allowed to come off under atmospheric conditions. (E)-methyl 2-[2-(6-(2-cyanophenoxy)pyrimidin-4-yloxy)phenyl]-3-methoxypropenoate was produced (39.4 area %). The reaction solution was then distilled under vacuum (20 mmHg) at 95° C. for 2 hours and at 120° C. for 1 hour. No further demethanolysis was evident. The reagents were cooled to 95° C. before an additional amount of potassium carbonate (45.6 g) was charged. The solution was again distilled under vacuum (20 mmHg) at 95° C. for 20 minutes and at 120° C. for 20 mins. (E)-Methyl 2-[2-(6-(2-cyanophenoxy)pyrimidin-4-yloxy)phenyl]-3-methoxypropenoate was produced (55.6 area %).

Provenance & Evidence