Reaktion #168708

Reaktionsgleichung

5-(3-bromo-phenyl)-5-hydroxymethyl-morpholin-3-one

DAST

Na2CO3

→

title compound

5-(3-Bromo-phenyl)-5-fluoromethyl-morpholin-3-one

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with dichloromethane
2. 2
   TrocknenThe extract was dried with sodium sulfate
3. 3
   Sonstigeevaporated

Vorschrift

A suspension of 5-(3-bromo-phenyl)-5-hydroxymethyl-morpholin-3-one (2.6 g, 9.09 mmol) and 120 ml of dichloromethane was cooled to 0° C. DAST (1.26 ml) was added dropwise. The mixture was stirred overnight, poured onto 50 ml of 10% aqueous Na2CO3 solution and ice and extracted with dichloromethane. The extract was dried with sodium sulfate and evaporated. Chromatography on silica gel (EtOAc/hexane=1:1) gave the title compound in the form of a colourless solid. TLC (hexane/EtOAc=1:1): Rf=0.31; HPLC: RtH2=3.13 min; 1H-NMR (400 MHz, CD3OD): 7.71 (s, 1H), 7.56 (d, 1H), 7.52 (d, 1H), 7.38 (t, 1H), 4.77 (d, 2H), 4.20 (s, 2H), 4.11 (d, 1H), 3.95 (d, 1H); MS: 289, 291 [(M+H)+].

Quelle