Hydrochloric Acid → 3-Bromo-5-chloro-2-fluorobenzenamine
Reaction equation
[Br:1][C:2]1[C:3]([F:17])=[C:4]([NH:9]C(=O)OC(C)(C)C)[CH:5]=[C:6]([Cl:8])[CH:7]=1.Cl>O1CCOCC1>[Br:1][C:2]1[C:3]([F:17])=[C:4]([CH:5]=[C:6]([Cl:8])[CH:7]=1)[NH2:9]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
tert-Butyl 3-bromo-5-chloro-2-fluorophenylcarbamate (1.0 g, 3.1 mmol) was treated with 4.0 M HCl in dioxane (10 mL) and the resulting reaction was maintained at room temperature for 4 hours. The reaction mixture was concentrated and partitioned between EtOAc (200 mL) and saturated aqueous NaHCO3 solution (75 mL). The layers were separated and the organic portion was washed with brine (75 mL), dried (Na2SO4), and concentrated to give 3-bromo-5-chloro-2-fluoroaniline as a colorless oil which was carried forward without further purification: LCMS (m/z) 225.9 (MH+), tR=0.96 minute; 1H NMR (400 MHz, CDCl3) δ 6.88 (m, 1H), 6.70 (d, J=7.0 Hz, 1H).