Ammonium Chloride → 5-Bromo-2-fluoroaniline

Temperature

100 °C

Iron powder (9.3 g, 0.166 mM) and ammonium chloride (1.7 g, 0.032 mM) were stirred in water (42 ml) at 100° C. for 30 minutes. Commercially available 2-nitro 4-bromo fluorobenzene (9.2 g, 0.42 mM) was added drop wise to the above solution over a period of 45 minutes. The reaction was stirred at 100° C. for an additional five hours. Water was removed in vacuo. The resultant crude solution was stirred in ethyl acetate (100 mL) for 20 minutes and the organic solution was decanted off. This wash was repeated two more times. The organic layers were combined, dried (MgSO4), passed through a plug of SiO2, and concentrated to afford 4.2 g (53% yield) of the desired product as a red oil. The product was used without further purification. NMR (CHCl3) δ 3.78 (bs, 2H); 6.65–7.07(m, 3H).

1. customWater was removed in vacuo
2. stirringThe resultant crude solution was stirred in ethyl acetate (100 mL) for 20 minutes
3. customthe organic solution was decanted off
4. dry with materialdried (MgSO4)
5. concentrationconcentrated

ORD record

ord-590a737312284d1cabcbdccfc2ed62ef

Source dataset

uspto-grants-2007_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07217730B2