Reacción #42381

Ecuación de reacción

methyl 3-bromo-5-(hydroxymethyl)benzoate

cesium carbonate

potassium carbonate

trimethyl boroxine

→

title compound

Methyl 3-(hydroxymethyl)-5-methylbenzoate

Disolventes

dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction mixture is refluxed for 5 h
2. 2
   Otropartitioned between water and ethyl acetate
3. 3
   LavadoThe organic layer is washed with water, saturated sodium bicarbonate, and brine
4. 4
   Secadodried (magnesium sulfate)
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated under reduced pressure
7. 7
   OtroPurification by flash column chromatography (silica, 20% ethyl acetate/hexanes)

Procedimiento

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]+.

Fuente