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

Temperature

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 record

ord-bf4b7c5e3ddc4c8abe351054238d0fa0

Source dataset

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07157447B2