反応 #69518

反応方程式

isoamyl nitrite

ethyl 4-amino-3-chloro-5-methoxybenzoate

acetonitrile

diiodomethane

→

title compound

収率 66.6%

Ethyl 3-chloro-4-iodo-5-methoxybenzoate

収率 66.6%

溶媒

n-heptane ethyl acetate

反応条件

後処理

1. 1
   workup.STIRRINGThe mixture was stirred at 70° C. for 40 minutes
2. 2
   その他was returned to room temperature
3. 3
   workup.DISTILLATIONthe solvent was then distilled off under reduced pressure
4. 4
   その他the residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate

実験手順

To ethyl 4-amino-3-chloro-5-methoxybenzoate (15.8 g, 68.8 mmol), were added acetonitrile (40 mL) and diiodomethane (22.2 mL, 275 mmol) in this order, and the mixture was stirred at 70° C., and then isoamyl nitrite (13.9 mL, 103 mmol) was added dropwise thereto over 10 minutes. The mixture was stirred at 70° C. for 40 minutes. The mixture was returned to room temperature, the solvent was then distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate: n-heptane/ethyl acetate=8/1 then 5/1) to obtain the title compound (15.6 g, 45.8 mmol)

出典