Hydrochloric Acid → HCID 57722994, compound

Participants

Reaction Steps

3-[4,6-Dibromo-2-(2-chlorophenyl)-3-pyridyl]propionic acid (1.09 g, 2.603 mmol) was dissolved in toluene (25 ml)-methanol (5 ml), and a 2M solution of trimethylsilyl-diazomethane in hexanes added (5 ml), and the solution allowed to stand for about 0.5 hours. The solution was evaporated in vacuo, and the resulting oil re-dissolved in dichloromethane (25 ml). This solution was added slowly at 22° to a trimethylaluminium-2-chloroaniline complex [prepared by adding 2M trimethylaluminium in toluene (2.6 ml) to a solution of 2-chloroaniline (0.55 ml, 5.188 mmol) in dichloromethane (30 ml)] and the solution stirred at 22° for 20 h under nitrogen. Water (15 ml) was added (very slowly at first), followed by sufficient 2M hydrochloric acid to dissolve all the precipitated aluminium salts. The organic phase was separated and the aqueous phase further extracted with dichloromethane (60 ml). The combined organic extracts were dried (Na2SO4), evaporated in vacuo, and the oily residue purified by column chromatography over silica (50 g) eluting with cyclohexane ethyl acetate (100:0-70:30) to afford the title compound as a gum (0.95 g, 69%).

Provenance & Evidence