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

Temperatur

0 °C

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 ethyl acetate 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%): 1H NMR (400 MHz, CDCl3): 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).

1. customdid not exceed 5° C
2. stirringthe mixture was stirred for an additional 1 h at this temperature
3. extractionThe mixture was extracted with ethyl acetate
4. washthe combined extracts were washed with brine
5. dry with materialdried over Na2SO4
6. concentrationThe filtrate was concentrated

ORD-Eintrag

ord-0a495bf5958f4dd6ba7302810e0e3052

Quelldatensatz

uspto-grants-2009_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07491819B1