Reacción #43602

Ecuación de reacción

1,2-dibromoethane

3-bromo-4,5-dihydroxybenzaldehyde

cesium carbonate

→

desired compound

Rendimiento 75.0%

8-Bromo-2,3-dihydro-1,4-benzodioxin-6-carbaldehyde

Rendimiento 75.0%

Disolventes

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter heating at 80° for 4 h
2. 2
   Otrothe dimethylformamide was removed under reduced pressure
3. 3
   OtroThe residue was partitioned between water and ethyl acetate
4. 4
   Lavadothe organic layer was washed with brine
5. 5
   Otrodried
6. 6
   OtroThe crude product was purified by flash column chromatography (silica gel, 4:1 hexane:ethyl acetate)

Procedimiento

To a solution of 3-bromo-4,5-dihydroxybenzaldehyde (11.5 g, 0.52 mol) in dimethylformamide (220 ml) was added cesium carbonate (50.7 g, 1.56 mol). The mixture was stirred at ambient temperature for 30 min, then 1,2-dibromoethane (12.76 g, 0.68 mol) were added. After heating at 80° for 4 h, the dimethylformamide was removed under reduced pressure. The residue was partitioned between water and ethyl acetate, and the organic layer was washed with brine and dried. The crude product was purified by flash column chromatography (silica gel, 4:1 hexane:ethyl acetate) to give the desired compound as an off-white solid (9.57 g, 75%).

Fuente