Hydrochloric Acid → 3-Bromo-5-chloro-2-fluorobenzenamine

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).

1. customthe resulting reaction
2. concentrationThe reaction mixture was concentrated
3. custompartitioned between EtOAc (200 mL) and saturated aqueous NaHCO3 solution (75 mL)
4. customThe layers were separated
5. washthe organic portion was washed with brine (75 mL)
6. dry with materialdried (Na2SO4)
7. concentrationconcentrated

ORD record

ord-d1c1705945b44971a8bdfe1f7d31ea8a

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08563553B2