2-Bromo-6-fluoroaniline → 1-Bromo-3-fluoro-2-nitrobenzene

Temperature

55 °C

To a suspension of sodium perborate tetrahydrate (135.374 g., 886.4 mmol) in 500 mL acetic acid at 55° C. was added dropwise a solution of 2-bromo-6-fluoro-phenylamine (33.685 g., 177.271 mmol) in 70 mL acetic acid over 1 hour. The reaction mixture was stirred at 55° C. for an additional 3 hours, then cooled to 0° C. in an ice bath. Insoluble materials were removed by filtration through a plug of celite, which was rinsed with 100 mL acetic acid. The combined acetic acid fractions were added to 3 L ice water with stirring to give a waxy solid which was removed by filtration. The crude solid was dissolved in 250 mL ethyl acetate, washed three times with 200 mL of 10% aqueous hydrogen chloride, 200 mL saturated sodium bicarbonate and 100 mL brine. The solution was concentrated in vacuo to give 11.51 g of 1-bromo-3-fluoro-2-nitro-benzene as a red oil,

1. temperaturecooled to 0° C. in an ice bath
2. customInsoluble materials were removed by filtration through a plug of celite, which
3. washwas rinsed with 100 mL acetic acid
4. additionThe combined acetic acid fractions were added to 3 L ice water
5. stirringwith stirring
6. customto give a waxy solid which
7. customwas removed by filtration
8. dissolutionThe crude solid was dissolved in 250 mL ethyl acetate
9. washwashed three times with 200 mL of 10% aqueous hydrogen chloride, 200 mL saturated sodium bicarbonate and 100 mL brine
10. concentrationThe solution was concentrated in vacuo

ORD record

ord-12ff75f9927648d8a3e214bba487a4fd

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07582760B2