Sodium Azide → 1-(Azidomethyl)-4-fluoro-2-iodobenzene

Participants

Reaction Conditions

Reaction Steps

A solution of 1-(bromomethyl)-4-fluoro-2-iodobenzene (M. Protiva et al., Collect. Czech. Chem. Comm., 44, 1979, 2108-2123) (17.9 g, 56.8 mmol) in N,N-dimethylformamide (35 ml) was treated with sodium azide (5.0 g, 76.7 mmol) and the resulting mixture was heated to 50° C. for 4 h. The cooled mixture was filtered, the filtrate was concentrated in vacuo and the residue was chromatographed on silica gel (elution hexane) to give 15.7 g (97% yield) of the title azide as a clear oil. 1HNMR 400 MHz (DMSO-d6) δ: 4.53 (2H, s), 7.32 (1H, m), 7.54 (1H, dd, J=6.0, 8.6 Hz), 7.83 (1H, dd, J=3.0, 8.0 Hz).

Provenance & Evidence