Sodium Iodide → 3-Nitrophenethyl azide

Participants

Reaction Steps

To a solution of 3-nitrophenethyl alcohol (2 g, 11.97 mmol), Et3N (3.0 mL, 20.8 mmol) in CH2Cl2 (40 mL) was added methanesulfonyl chloride (1.0 mL, 12.9 mmol) at 0° C. After stirring for 0.5 hr, more CH2Cl2 was added. The solution was washed with water and brine, dried over Na2SO4 and concentrated. The residue was dissolved in DMF (30 mL), sodium azide (0.8 g,12.3 mmol), lithium chloride (0.53 g, 12.5 mmol) and catalytic amount of sodium iodide were added. The mixture was stirred at room temperature overnight. Most of DMF was then removed under vacuum and the residue was washed with water and brine, dried over Na2SO4 and concentrated. The residue was chromatographed over silica gel (eluent: hexane:ethyl acetate v/v 4:1) to give a pale yellow oil (1.8 g) as desired product.

Provenance & Evidence