Hydrochloric Acid → HCID 22221088, compound

Participants

Reaction Steps

To a solution of ethyl 5-(3-bromo-4-chlorophenyl)isoxazole-4-carboxylate (6.19 g) in tetrahydrofuran (100 ml) was gently added diisobutylaluminum hydride (1.0 M tetrahydrofuran solution, 40 ml) at 0° C. and the mixture was stirred at room temperature for 30 min. The reaction mixture was poured into dilute hydrochloric acid, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated to give 5-(3-bromo-4-chlorophenyl)-4-isoxazolylmethanol (5.10 g, yield 94%) as a colorless oil. NMR (CDCl3) δ: 4.73 (2H, d, J=4.8 Hz), 7.59 (1H, d, J=8.4 Hz), 7.72 (1H, dd, J=2.2, 8.4 Hz), 8.10 (1H, d, J=2.2 Hz), 8.37 (1H, s).

Provenance & Evidence