تفاعل #81406

معادلة التفاعل

pyridine

5-phenyl-8-methyl-2-oxobenzazepine

phosphorus pentachloride

sodium bisulfite

bromine

→

product

المردود 49.2%

3-Bromo-2-oxo-5-phenyl-2,3,4,5-tetrahydro-1H-(1)benzazepine

المردود 49.2%

المذيبات

dichloromethane

methylene chloride

methylene chloride

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added
2. 2
   أخرىthe reaction)
3. 3
   درجة الحرارةto warm quickly (10 minutes) to 0° C.
4. 4
   تجفيفThe organic phase was then dried over sodium sulfate
5. 5
   أخرىevaporated
6. 6
   ترشيحfiltered
7. 7
   workup.DISSOLUTIONthe solid dissolved

الإجراء التجريبي

To a 200 mL three neck round-bottomed flask equipped with a nitrogen inlet and septum were added 5.48 grams (21.8 mmol) 5-phenyl-8-methyl-2-oxobenzazepine, 100 mL dichloromethane, and 4.55 grams (21.8 mmol) phosphorus pentachloride. After dissolution, 1.85 mL (22.9 mmol) pyridine was added, and the solution cooled to -70° C. To the stirring solution (some precipitate appeared at this temperature, but did not affect the reaction) was added a solution of 1.12 mL (21.8 mmol) bromine in 10 mL methylene chloride dropwise over 20 minutes. The reaction was then allowed to warm quickly (10 minutes) to 0° C., and 50 mL of saturated aqueous sodium bisulfite solution was added. The reaction was then diluted with methylene chloride and allowed to stand under sodium bisulfite solution with periodic shaking for 2 hours, until the organic phase no longer exhibited a reddish color. The organic phase was then dried over sodium sulfate and evaporated. The residue was suspended in methylene chloride and filtered, and the solid dissolved to afford 3.39 grams (47%) of product as a white solid. The filtrate was adsorbed onto silica gel and chromatographed using 7:3 hexane/ethyl acetate as eluant to afford additional product as a white solid, 1.38 g, total 5.14 (71%).

المصدر