Reacción #67302

Ecuación de reacción

1-(5-bromo-3-chloro-2-hydroxyphenyl)ethanone

(2R)-(−)Glycidyltosylate

K2CO3

water

→

title compound

Rendimiento 74.7%

1-[5-BROMO-3-CHLORO-2-(OXIRAN-2-YLMETHOXY)PHENYL]ETHANONE

Rendimiento 74.7%

Disolventes

DMF

EtOAc

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowas brought to ambient temperature
2. 2
   ExtracciónThe water phase was extracted with EtOAc
3. 3
   LavadoThe combined organic phases were washed with LiCl (5%), HCl (1 N) and brine
4. 4
   Secadodried (Na2SO4)
5. 5
   Otroevaporated to dryness
6. 6
   OtroPurification on flash column chromatography (isooctane/EtOAc)

Procedimiento

A mixture of 1-(5-bromo-3-chloro-2-hydroxyphenyl)ethanone (5.5 g, 21.9 mmol), (2R)-(−)Glycidyltosylate (10 g, 43.8 mmol) and K2CO3 (4.5 g, 32.9 mmol) in DMF (25 ml) was heated at 60° C. for 25 h. The solution was brought to ambient temperature and water and EtOAc was added. The water phase was extracted with EtOAc. The combined organic phases were washed with LiCl (5%), HCl (1 N) and brine and then dried (Na2SO4) and evaporated to dryness. Purification on flash column chromatography (isooctane/EtOAc) gave the title compound (5.0 g). MS m/z (rel. intensity, 70 eV) 250 (30), 248 (M+, 26), 235 (bp), 233 (85), 57 (90), 306 (M+, 9).

Fuente