反应 #806307

反应方程式

1-(4-chloro-phenyl)-3-cyclopentyl-propan-1-one O-methyl-oxime

N-bromosuccinimide

benzoyl peroxide

→

2-bromo-1-(4-chloro-phenyl)-3-cyclopentyl-propan-1-one O-methyl-oxime

收率 80.0%

溶剂

carbon tetrachloride

反应条件

后处理

1. 1
   温度The resulting mixture was heated
2. 2
   温度at reflux for 12 h
3. 3
   过滤the solids were filtered
4. 4
   洗涤washed with diethyl ether
5. 5
   洗涤The filtrate was washed with aqueous solution of sodium bicarbonate, sodium thiosulfate and brine
6. 6
   干燥It was then dried with anhydrous sodium sulfate
7. 7
   浓缩concentrated in vacuo
8. 8
   其他Purification of the crude residue by flash chromatography (Biotage system, KP-Sil™ 32–63 μm, 60 Å silica gel)
9. 9
   洗涤eluting with 1–2% ethyl acetate in hexanes

实验过程

To a solution of 1-(4-chloro-phenyl)-3-cyclopentyl-propan-1-one O-methyl-oxime (1.120 g, 4.214 mmol) in carbon tetrachloride were added N-bromosuccinimide (812 mg, 4.425 mmol) and benzoyl peroxide (102 mg, 0.4 mmol). The resulting mixture was heated at reflux for 12 h. Upon cooling to room temperature, the solids were filtered and washed with diethyl ether. The filtrate was washed with aqueous solution of sodium bicarbonate, sodium thiosulfate and brine. It was then dried with anhydrous sodium sulfate and concentrated in vacuo. Purification of the crude residue by flash chromatography (Biotage system, KP-Sil™ 32–63 μm, 60 Å silica gel) eluting with 1–2% ethyl acetate in hexanes yielded 2-bromo-1-(4-chloro-phenyl)-3-cyclopentyl-propan-1-one O-methyl-oxime (1.16 g, 80%) as yellow oil.

来源