Reacción #161511

Ecuación de reacción

Cycloheptylmethanol

3-bromophenol

→

((3-bromophenoxy)methyl)cycloheptane

Condiciones de reacción

Tratamiento posterior

1. 1
   ConcentraciónAfter concentration under reduced pressure, hexanes
2. 2
   workup.ADDITIONwas added
3. 3
   Otrosonicated
4. 4
   Otrothe precipitate was removed by filtration
5. 5
   Lavadothe solids washed with hexanes
6. 6
   ConcentraciónThe combined filtrates were concentrated under reduced pressure
7. 7
   OtroPurification by flash chromatography (10 to 50% EtOAc-hexanes gradient)

Procedimiento

Cycloheptylmethanol was coupled with 3-bromophenol following the method used in Example 10. After concentration under reduced pressure, hexanes was added. The mixture was stirred and sonicated then the precipitate was removed by filtration and the solids washed with hexanes. The combined filtrates were concentrated under reduced pressure. Purification by flash chromatography (10 to 50% EtOAc-hexanes gradient) gave ((3-bromophenoxy)methyl)cycloheptane. (Yield 1.0697 g, 56%): 1H NMR (400 MHz, CDCl3) δ 7.12 (t, J=8.4, 1H), 7.06-7.04 (m, 2H), 6.82 (dq, J=8.0, 1.2, 1H), 3.70 (d, J=6.4, 2H), 1.91-1.98 (m, 1H), 1.81-1.88 (m, 2H), 1.42-1.72 (m, 8H), 1.24-1.34 (m, 2H).

Fuente