반응 #69518

반응 방정식

isoamyl nitrite

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

acetonitrile

diiodomethane

→

title compound

수율 66.6%

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

수율 66.6%

용매

n-heptane ethyl acetate

반응 조건

후처리

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

실험 절차

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)

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