反応 #45563

反応方程式

potassium carbonate

trimethylboroxine

4-bromo-2-fluoro-6-nitroanisole

sodium bicarbonate water

→

compound

収率 73.5%

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

収率 73.5%

溶媒

1,4-dioxane

反応条件

後処理

1. 1
   温度with heating
2. 2
   温度under reflux for 1 hour
3. 3
   抽出followed by extraction three times with ethyl acetate
4. 4
   洗浄the organic layer was washed with saturated brine
5. 5
   乾燥dried over anhydrous magnesium sulfate
6. 6
   ろ過After filtration and concentration under reduced pressure
7. 7
   濃縮the eluate with n-hexane:ethyl acetate (20:1) was concentrated under reduced pressure

実験手順

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.

出典