ChemicalBook CAS DataBase List 2-Bromo-5-fluoroaniline

2-Bromo-5-fluoroaniline synthesis

8synthesis methods

Product Name:2-Bromo-5-fluoroaniline
CAS Number:1003-99-2
Molecular formula:C6H5BrFN
Molecular Weight:190.01

446-09-3 Synthesis

446-09-3
238 suppliers
$7.00/5g

1003-99-2
302 suppliers
$6.00/5g

Yield:1003-99-2 100%

Reaction Conditions:

Stage #1:2-bromo-5-fluoronitrobenzene with iron;acetic acid in ethanol at 20; for 2.08333 h;Heating / reflux;
Stage #2: with sodium hydroxide in diethyl ether;water

Steps:

2-Bromo-5-fluorobenzenamine; To a solution of 1-bromo-4-fluoro-2-nitrobenzene (5.0 g, 22.7 mmol) in HOAc/EtOH (20 mL/20 mL) was added iron powder in one portion at room temperature. The mixture was bubbled with N₂for 5 min, and then refluxed for 2 hrs. Partial of the solvents were removed on rotary vacuum, then the residue was partitioned between aqueous NaOH (10N, 200 mL) and Et₂O (200mL). After separation, the organic phase was washed with H₂O(50 mL), brine (50 mL), dried on MgSO₄, and concentrated on rotary vacuum to afford the expected product, as an light tan oil (quantitative yield), which was pure enough to be used in next step without further purification; ¹H NMR (400 MHz, CDCl₃) δ ppm 4.15 (s, 1 H), 6.34 (td, J=8.44, 2.77 Hz, 1 H) ,6.46 (dd, J=10.20, 2.90 Hz, 1 H), 7.31 (dd, J=8.81, 5.79 Hz, 1 H); Mass spec. 189.94 (MH⁺), Calc. for C₆H₅BrFN 188.96.

References:

Bristol-Myers Squibb Company US2007/259850, 2007, A1 Location in patent:Page/Page column 95-96

FullText