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 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).

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 EtOAc
4. washthe combined extracts were washed with brine
5. dry with materialdried over Na2SO4
6. concentrationThe filtrate was concentrated

ORD record

ord-3366782b1133429080050de0f0298188

Source dataset

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08039458B2