Potassium Iodide → (3-Iodo-quinolin-6-yloxy)-methoxy-acetic acid methyl ester

Participants

Reaction Steps

To a solution of potassium t-butoxide (1.36 g) in t-butyl alcohol (50 mL) was added a solution of 3-iodo-quinolin-6-ol (3 g) in t-butyl alcohol (5 mL). The reaction mixture was stirred at room temperature for 15 minutes. Bromo-methoxy-acetic acid methyl ester (4.0 g) and a solution of potassium iodide (catalytic quantity) in t-butyl alcohol (5 mL) were then added. The reaction mixture was stirred at room temperature for 18 hours. The mixture was poured on water and chloroform was added. The mixture was stirred. The two layers were separated, the aqueous layer was extracted with chloroform (twice). The organic layers were combined, washed with brine (twice), dried over sodium sulphate, filtered and concentrated under reduced pressure. The crude (4.3 g) was used directly in the next step without purification.

Provenance & Evidence