Reaktion #67302

Reaktionsgleichung

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

(2R)-(−)Glycidyltosylate

K2CO3

water

→

title compound

Ausbeute 74.7%

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

Ausbeute 74.7%

Lösungsmittel

DMF

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas brought to ambient temperature
2. 2
   ExtraktionThe water phase was extracted with EtOAc
3. 3
   WaschenThe combined organic phases were washed with LiCl (5%), HCl (1 N) and brine
4. 4
   Trocknendried (Na2SO4)
5. 5
   Sonstigeevaporated to dryness
6. 6
   SonstigePurification on flash column chromatography (isooctane/EtOAc)

Vorschrift

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).

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