반응 #45563

반응 방정식

potassium carbonate

trimethylboroxine

4-bromo-2-fluoro-6-nitroanisole

sodium bicarbonate water

→

compound

수율 73.5%

1-Fluoro-2-methoxy-5-methyl-3-nitrobenzene

수율 73.5%

용매

1,4-dioxane

반응 조건

후처리

1. 1
   온도with heating
2. 2
   온도under reflux for 1 hour
3. 3
   추출followed by extraction three times with ethyl acetate
4. 4
   세척the organic layer was washed with saturated brine
5. 5
   건조dried over anhydrous magnesium sulfate
6. 6
   여과After filtration and concentration under reduced pressure
7. 7
   농축the eluate with n-hexane:ethyl acetate (20:1) was concentrated under reduced pressure

실험 절차

Under nitrogen atmosphere, potassium carbonate (218 mg, 1.58 mmol), tetrakistriphenylphosphine palladium(0) (58 mg, 50 μmol), trimethylboroxine (77 μl, 0.55 mmol) were added to a 1,4-dioxane (5 ml) solution of 4-bromo-2-fluoro-6-nitroanisole (125 mg, 0.5 mmol), followed by stirring with heating under reflux for 1 hour and a half. After cooling to room temperature, saturated sodium bicarbonate water was added to the reaction liquid, followed by extraction three times with ethyl acetate, the organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate. After filtration and concentration under reduced pressure, the resulting residue was subjected to column chromatography, and the eluate with n-hexane:ethyl acetate (20:1) was concentrated under reduced pressure to obtain the entitled compound (68 mg, 70%) as an orange oily substance.

출처