Reaction #79871

Reaction equation

4-bromo-2-fluoroaniline

2-chlorobenzoxazole

→

N2-(4-bromo-2-fluorophenyl)-1,3-benzoxazol-2-amine

Yield 92.0%

Conditions

Workup

1. 1
   TemperatureThe purple solution was heated
2. 2
   Temperatureat reflux for 30 min.
3. 3
   Filtrationthe precipitate was filtered
4. 4
   WashThe filter cake was washed with five 2-mL portion of heptane

Procedure

To a solution of 4-bromo-2-fluoroaniline 1.00 g, 5.26 mmol) in toluence (25 mL) was added 2-chlorobenzoxazole (0.66 mL, 5.79 mmol, 1.1 equiv). The purple solution was heated at reflux for 30 min. and then at 100° C. for 17 hours. The resulting white suspension/purple solution was cooled to room temperature and the precipitate was filtered. The filter cake was washed with five 2-mL portion of heptane to afford N2-(4-bromo-2-fluorophenyl)-1,3-benzoxazol-2-amine (1.480 g, 92%) as a light purple powder. RP-HPLC (25 to 100% CH3CN in 0.1 N aqueous ammonium acetate over 10 minutes at 1 mL/min using a Hypersil HS C18, 250×4.6 mm column) tr=12.87 min., 97%; and m/z 306.7(MH+).

Source