反应详情

A mixture of isopropenyl acetate (12.2 g, 122 mmol), 2,4,6-trichloroaniline (16.0 g, 81.4 mmol), potassium carbonate (100 mg, 0.7 mmol), and acetone (100 g) was cooled to 10° C. tert-Butyl nitrite (90%, 10 g, 87.3 mmol) was dosed over 30 minutes. The reaction was stirred for further 90 minutes, and it was concentrated to a black oil. The residue was triturated with water, and the pH was adjusted to 10.5 with sodium hydroxide solution. The precipitate was filtered and recrystallized from methanol-water 1:1. The solid was filtered, washed with methanol-water 1:1, and dried. The product was obtained as dark-brown crystalline material (15.9 g, 70.7% purity, 47.3 mmol, 58% yield). Further purification was achieved by recrystallization from hexanes. 1H NMR (400 MHz, CDCl3): δ 2.23 (s, 3H, CH3), 4.02 (s, 2H, CH2), 7.31 (s, 2H, CH).

1. concentrationit was concentrated to a black oil
2. customThe residue was triturated with water
3. filtrationThe precipitate was filtered
4. customrecrystallized from methanol-water 1:1
5. filtrationThe solid was filtered
6. washwashed with methanol-water 1:1
7. customdried
8. customThe product was obtained as dark-brown crystalline material (15.9 g, 70.7% purity, 47.3 mmol, 58% yield)
9. customFurther purification
10. customwas achieved by recrystallization from hexanes