Reacción #159785

Ecuación de reacción

(2-bromo-5-iodo-phenyl)-chroman-6-yl-methanone

triethylsilane

→

6-(2-bromo-5-iodo-benzyl)-chroman

Rendimiento 77.5%

Disolventes

acetonitrile dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroreaction
2. 2
   Otrowas quenched by the addition of saturated aqueous sodium bicarbonate solution
3. 3
   OtroVolatiles were evaporated under reduced pressure
4. 4
   ExtracciónThe aqueous layer was extracted with ethyl acetate (2×20 mL)
5. 5
   LavadoEthyl acetate layer was washed with water, brine
6. 6
   Secadodried over sodium sulfate
7. 7
   Concentraciónconcentrated
8. 8
   Otropurified by silica gel column chromatography

Procedimiento

To a stirred solution of (2-bromo-5-iodo-phenyl)-chroman-6-yl-methanone (2.0 g, 4.51 mmol) in acetonitrile: dichloromethane (2:1 mixture, 9 mL) was added triethylsilane (2.52 mL, 15.78 mmol) and boron trifluoride diethyl etherate complex 1.11 mL, 9.02 mmol) at 0° C. After stirring overnight at room temperature, reaction was quenched by the addition of saturated aqueous sodium bicarbonate solution. Volatiles were evaporated under reduced pressure. The aqueous layer was extracted with ethyl acetate (2×20 mL). Ethyl acetate layer was washed with water, brine, dried over sodium sulfate, concentrated and purified by silica gel column chromatography to furnish 6-(2-bromo-5-iodo-benzyl)-chroman (1.5 g).

Fuente