Reacción #9333

Ecuación de reacción

NH4Cl

4-bromobenzyl alcohol

NaH

4-methoxybenzyl chloride

→

7-2

Rendimiento 98.0%

4-Bromobenzyl (4-methoxybenzyl) ether

Rendimiento 98.0%

Disolventes

THF

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITAfter 24 h
2. 2
   ExtracciónThe resulting mixture was extracted with ethyl acetate (3×60 mL)
3. 3
   Lavadothe combined ethyl acetate solution was washed with water and brine
4. 4
   SecadoThe solution was then dried (Na2SO4)
5. 5
   Filtraciónfiltered
6. 6
   Otroevaporated
7. 7
   OtroPurification of the residue by flash chromatography on silica gel (5% ethyl acetate/hexanes)

Procedimiento

A solution of 4-bromobenzyl alcohol (2.011 g, 10.7 mmol) in THF (42 mL) was added to a mixture of NaH (663 mg, 16.6 mmol, 60% in oil) in DMF (13 mL). The mixture was stirred for 1.5 h and 4-methoxybenzyl chloride (MPMCl, 2 mL, 14.8 mmol) was added. After 24 h, 100 mL saturated NH4Cl solution was added. The resulting mixture was extracted with ethyl acetate (3×60 mL) and the combined ethyl acetate solution was washed with water and brine. The solution was then dried (Na2SO4), filtered and evaporated. Purification of the residue by flash chromatography on silica gel (5% ethyl acetate/hexanes) gave 7-2 (2.43 g, 98%).

Fuente