Reacción #67282

ord-c4f7e5f0653e424aadb321dbd738c539

Ecuación de reacción

CC(=O)c1cc(Br)cc(F)c1O
1-(5-bromo-3-fluoro-2-hydroxyphenyl)ethanone
Cc1ccc(S(=O)(=O)OC[C@H]2CO2)cc1
(R)-glycidyltosylate
O=C([O-])[O-].[K+].[K+]
K2CO3
→
CC(=O)c1cc(Br)cc(F)c1OC[C@H]1CO1
title compound
Rendimiento 39.9%
CC(=O)c1cc(Br)cc(F)c1OC[C@H]1CO1
1-(5-BROMO-3-FLUORO-2-[(2R)-OXIRAN-2-YLMETHOXY]PHENYL) ETHANONE
Rendimiento 39.9%

Reactantes

CC(=O)c1cc(Br)cc(F)c1O
1-(5-bromo-3-fluoro-2-hydroxyphenyl)ethanone
Cc1ccc(S(=O)(=O)OC[C@H]2CO2)cc1
(R)-glycidyltosylate
O=C([O-])[O-].[K+].[K+]
K2CO3

Reactivos

Ninguno

Disolventes

CN(C)C=O
DMF

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroPreparation
  2. 2
    LavadoThe combined organic phases were washed with LiCl (5%), HCl (1 N)

Procedimiento

Preparation according to Preparation 1 using 1-(5-bromo-3-fluoro-2-hydroxyphenyl)ethanone (16.8 g, 72 mmol), (R)-glycidyltosylate (18.1 g, 79 mmol), K2CO3 (15.0 g, 108 mmol) and DMF (60 ml). The combined organic phases were washed with LiCl (5%), HCl (1 N). Flash column chromatography (isooctane/EtOAc) yielded the title compound (8.3 g). MS m/z (rel. intensity, 70 eV) 290 (M+, 9), 288 (M+, 9), 217 (bp), 81 (47), 57 (46).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08524766B2uspto-grants-2013_09