Reacción #2314278

Ecuación de reacción

tetrabromomethane

3-(4-hydroxyphenyl)-1-propanol

triphenylphosphine

→

3-(4-hydroxyphenyl)-1-bromopropane

Rendimiento 62.0%

Disolventes

dichloromethane

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted with dichloromethane
2. 2
   Lavadothe organic layer was washed with water
3. 3
   Secadodried over anhydrous magnesium sulfate
4. 4
   OtroThe solvent was removed in vacuo
5. 5
   Otrothe crude reaction mixture
6. 6
   Filtraciónwas filtered through silica gel
7. 7
   Lavadoeluting with 10% ethyl acetate in hexane

Procedimiento

A solution of tetrabromomethane (1.125 eq.) in dichloromethane (0.5 ml/mole) was added dropwise to the solution of the commercially available 3-(4-hydroxyphenyl)-1-propanol 1B (1 eq.) and triphenylphosphine (1.125 eq.) in dichloromethane at 0° C. The reaction mixture was stirred at room temperature for 2 days, extracted with dichloromethane, and the organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed in vacuo. the crude reaction mixture was filtered through silica gel, eluting with 10% ethyl acetate in hexane, to give 3-(4-hydroxyphenyl)-1-bromopropane 2 as a brown oil in 62% yield.

Fuente