Sodium Azide → 2-Azido-1-bromo-4-fluorobenzene

Participants

Reaction Conditions

Reaction Steps

2-Bromo-5-fluoro aniline (2.00 g, 10.53 mmol) was dissolved in concentrated HCl (10 mL) and water (10 mL) and cooled to 0° C. Aqueous NaNO2 solution (1.090 g, 15.8 mmol of NaNO2 in 10 mL of water) was added dropwise at such a rate that the temperature did not exceed 5° C. This mixture was stirred at 0° C. for 1.5 h. A solution of NaN3 (1.027 g, 15.8 mmol) and NaOAc (12.95 g, 158 mmol) in water (50 mL) was then added at 0-5° C. and the mixture was stirred for an additional 1 h at this temperature. The mixture was extracted with EtOAc and the combined extracts were washed with brine and dried over Na2SO4. The filtrate was concentrated to afford the title compound as a tan solid (2.188 g, 96% yield): 1H NMR (400 MHz, CDCl3) δ: 7.53 (1H, dd, J=8.8, 5.6 Hz), 6.94 (1H, dd, J=8.8, 2.8 Hz), 6.79 (1H, ddd, J=8.8, 7.6, 2.8 Hz).

Provenance & Evidence