2-Chlorobenzoxazole → N2-(4-bromo-2-fluorophenyl)-1,3-benzoxazol-2-amine
Reaktionsgleichung
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([F:9])[CH:3]=1.Cl[C:11]1[O:12][C:13]2[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=2[N:15]=1>>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:11]2[O:12][C:13]3[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=3[N:15]=2)=[C:4]([F:9])[CH:3]=1Komponenten
3
Versuchsvorschrift
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+).