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) is added methanesulfonyl chloride (1.0 mL, 12.9 mmol) at 0° C. After stirring for 0.5 hr, more CH2Cl2 is added. The solution is washed with water and brine, dried over Na2SO4 and concentrated. The residue is 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 are added. The mixture is stirred at room temperature overnight. Most of DMF is then removed under vacuum and the residue is washed with water and brine, dried over Na2SO4 and concentrated. The residue is 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