反応 #42381

反応方程式

methyl 3-bromo-5-(hydroxymethyl)benzoate

cesium carbonate

potassium carbonate

trimethyl boroxine

→

title compound

Methyl 3-(hydroxymethyl)-5-methylbenzoate

溶媒

dioxane

反応条件

後処理

1. 1
   温度The reaction mixture is refluxed for 5 h
2. 2
   その他partitioned between water and ethyl acetate
3. 3
   洗浄The organic layer is washed with water, saturated sodium bicarbonate, and brine
4. 4
   乾燥dried (magnesium sulfate)
5. 5
   ろ過filtered
6. 6
   濃縮concentrated under reduced pressure
7. 7
   その他Purification by flash column chromatography (silica, 20% ethyl acetate/hexanes)

実験手順

To a stirred solution of methyl 3-bromo-5-(hydroxymethyl)benzoate (3.0 g, 12.2 mmol) in dioxane (27 mL) is added cesium carbonate (4.0 g, 12.2 mmol), potassium carbonate (34 g, 24.4 mmol), and palladium(0)tetrakis(triphenylphosphine) (704 mg, 0.61 mmol), followed by trimethyl boroxine (1.7 mL, 12.2 mmol). The reaction mixture is refluxed for 5 h, cooled to room temperature, and then partitioned between water and ethyl acetate. The organic layer is washed with water, saturated sodium bicarbonate, and brine, dried (magnesium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 20% ethyl acetate/hexanes) provides the title compound. ESI MS m/z 181.2 [M+H]+.

出典