Reaktion #328984

Reaktionsgleichung

2-amino-3-nitrophenol

2-chloro-1,1,1-triethoxyethane

→

desired product

Ausbeute 17.9%

2-(Chloromethyl)-4-nitrobenzo[d]oxazole

Ausbeute 17.9%

Lösungsmittel

2-methoxyethylether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto reflux overnight
2. 2
   Sonstigethe solvent was removed in vacuo
3. 3
   Filtrationfiltered

Vorschrift

To a RT solution of 2-amino-3-nitrophenol (14.7 g, 95 mmol, 1.0 equiv) in 2-methoxyethylether (136 mL) was added 2-chloro-1,1,1-triethoxyethane (19.1 g, 97.3 mmol, 1.02 equiv) and p-toluene sulfonic acid hydrate (25 mg, 0.13 mmol, 0.2 equiv). The resulting mixture was heate to reflux overnight. After the reaction was cooled to RT, the solvent was removed in vacuo. The solid was suspended in methanol (40 mL), stirred and filtered to provide the desired product as a red solid (3.61 g). The filtrate provided an additional 9.8 g of the title compound through an additional methanol treatment (13.4 g, 98% combined).

Quelle