تفاعل #77659

معادلة التفاعل

N-[2-(4-acetyl-phenyl)-ethyl]-acetamide

methanol

Tetrabutylammonium tribromide

→

pure product

المردود 83.0%

N-[2-(4-Bromoacetyl-phenyl)-ethyl]-acetamide

المردود 83.0%

المذيبات

methylene chloride

methylene chloride

ظروف التفاعل

المعالجة

1. 1
   أخرىThe volatiles were then removed in vacuo
2. 2
   أخرىto afford an oil, which
3. 3
   استخلاصextracted with 125 ml of saturated aqueous sodium bicarbonate
4. 4
   غسيلthe combined organic extracts were then washed with water
5. 5
   تجفيفdried over magnesium sulfate
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated in vacuo
8. 8
   أخرىThe crude oil was purified by column chromatography (silica gel; methylene chloride to 7% methanol/methylene chloride)
9. 9
   غسيلthe resulting material was washed with 110 ml of water

الإجراء التجريبي

In a round-bottomed flask, N-[2-(4-acetyl-phenyl)-ethyl]-acetamide (7.23 g, 35.2 mmol) was dissolved in methylene chloride (120 ml), and methanol (60 ml). Tetrabutylammonium tribromide (17.0 g, 35.2 mmol) was added to this solution in one portion, and the mixture was allowed to stir overnight at room temperature. The volatiles were then removed in vacuo to afford an oil, which was then resuspended in 100 ml of methylene chloride and extracted with 125 ml of saturated aqueous sodium bicarbonate. The aqueous extracts were reextracted with methylene chloride (3×100 ml), and the combined organic extracts were then washed with water, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude oil was purified by column chromatography (silica gel; methylene chloride to 7% methanol/methylene chloride), and the resulting material was washed with 110 ml of water to afford 8.27 g (83% yield) of pure product as a white solid. LRMS ([M−1]−)=283.0, 284.9.

المصدر