تفاعل #77669

معادلة التفاعل

tetrabutylamonium tribromide

Benzyl-[2-(4-acetyl-phenoxy)-ethyl]-carbamate

→

Benzyl-[2-(4-bromoacetylphenoxy)-ethyl]-carbamate

المردود 90.0%

المذيبات

methanol

methylene chloride

ظروف التفاعل

المعالجة

1. 1
   أخرىquenched with water
2. 2
   استخلاصThe aqueous phase was extracted with ethyl acetate
3. 3
   غسيلwashed with saturated aqeous sodium bicarbonate, and saturated Na2S2O3
4. 4
   تجفيفThe combined organic extracts were dried over magnesium sulfate
5. 5
   ترشيحfiltered
6. 6
   تركيزconcentrated in vacuo
7. 7
   أخرىthe resulting crude material was purified by column chromatography (silica gel; hexanes to 2:1 hexanes/ethyl acetate)
8. 8
   أخرىto afford a colorless oil which

الإجراء التجريبي

Benzyl-[2-(4-acetyl-phenoxy)-ethyl]-carbamate (10.2 g, 32.5 mmol) was dissolved in methylene chloride (100 ml) and methanol (50 ml), and tetrabutylamonium tribromide (15.7 g, 32.5 mmol) was added in one portion. The reaction mixture was stirred for about sixteen hours, and then quenched with water. The aqueous phase was extracted with ethyl acetate and then washed with saturated aqeous sodium bicarbonate, and saturated Na2S2O3. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated in vacuo, and the resulting crude material was purified by column chromatography (silica gel; hexanes to 2:1 hexanes/ethyl acetate) to afford a colorless oil which solidified upon standing. (11.5 g, 90% yield).

المصدر