Tetrahydrofuran → 3-Bromo-5-(bromoacetyl)isoxazole

Participants

Reaction Steps

A mixture of 3-bromo-5-acetylisoxazole (which was obtained in Example 117) (16.7 g, 87.9 mmol), phenyltrimethylammonium tribromide (33.4 g, 88.8 mmol) and tetrahydrofuran (150 mL) was stirred at ambient temperature for 18 hours, poured into water and extracted with ether. The organic extracts were washed with brine and dried over MgSO4. Evaporation and purification by distillation gave a light yellow oil (8.9 g, 40% yield); 1H NMR (300 MHz, CDCl3) δ 4.40. (s, 3H), 7.10 (s, 1H).

Provenance & Evidence