Reaktion #961065

Reaktionsgleichung

3,7-dimethylbenzo[d]isoxazole

HNO3

→

title product

Ausbeute 73.0%

3,7-dimethyl-5-nitrobenzo[d]isoxazole

Ausbeute 73.0%

Lösungsmittel

water

H2SO4

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled down
2. 2
   workup.STIRRINGthe resulting mixture was stirred at 0° C. for 1 hr
3. 3
   Extraktionextracted three times with CH2Cl2
4. 4
   WaschenThe combined organic layers were washed with NaHCO3 solution and brine
5. 5
   Trocknendried over MgSO4
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated under reduced pressure
8. 8
   SonstigeThe resulting yellow solid was triturated with Et2O
9. 9
   Filtrationfiltrated off
10. 10
    Waschenwashed with Et2O
11. 11
    Sonstigedried

Vorschrift

3,7-dimethylbenzo[d]isoxazole (Step 46.4) (2 g, 12.77 mmol) was dissolved in H2SO4 (5 mL), cooled down and stirred at 0° C. HNO3 (0.878 mL, 12.77 mmol) was slowly added and the resulting mixture was stirred at 0° C. for 1 hr. The reaction was diluted with water (60 mL) and extracted three times with CH2Cl2. The combined organic layers were washed with NaHCO3 solution and brine, dried over MgSO4, filtered and concentrated under reduced pressure. The resulting yellow solid was triturated with Et2O, filtrated off, washed with Et2O and dried to afford the title product (1.86 g, 9.29 mmol, 73% yield) as yellow solid. tR: 0.98 min (LC-MS 2); ESI-MS: 193 [M+H]+.

Quelle