反応 #5487

反応方程式

bromine

Phosphorus pentachloride

iodine

Ethyl 2-oxo-1-azacyclodecane-10-carboxylate

→

cis ethyl 3-bromo-2-oxo-1-azacyclodecane-10-carboxylate

溶媒

methylene chloride

反応条件

後処理

1. 1
   workup.STIRRINGthe reaction is stirred at 0° C. for 4 hours
2. 2
   その他The reaction is quenched
3. 3
   workup.ADDITIONby adding saturated sodium sulfite (until the color of excess bromine
4. 4
   抽出extracted several times with methylene chloride
5. 5
   乾燥The combined organic layers are dried (Na2SO4)
6. 6
   その他the solvent is evaporated
7. 7
   その他The product is purified by silica gel chromatography (15% ethyl acetate/hexane)

実験手順

Ethyl 2-oxo-1-azacyclodecane-10-carboxylate (4.0 g, 17.6 mmol) is dissolved in methylene chloride (50 mL), and cooled to 0° C. Phosphorus pentachloride (3.85 g, 18.5 mmol) and iodine (0.051 g, 0.2 mmol) are added. The reaction is stirred for 15 minutes at 0° C. Then, bromine (3.10 g, 19.4 mmol) is added, and the reaction is stirred at 0° C. for 4 hours. The reaction is quenched by adding saturated sodium sulfite (until the color of excess bromine disappears), and extracted several times with methylene chloride. The combined organic layers are dried (Na2SO4), and the solvent is evaporated. The product is purified by silica gel chromatography (15% ethyl acetate/hexane) to give cis ethyl 3-bromo-2-oxo-1-azacyclodecane-10-carboxylate, m.p. 132°-134° C.

出典