Reaktion #52675

Reaktionsgleichung

diethylazodicarboxylate

Triphenylphosphine

3-bromo-4-hydroxybenzaldehye

2-hydroxyethylmorpholine

→

4-morpholinoethoxy-3-bromobenzaldehyde

Ausbeute 56.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenthe reaction was concentrated under reduced pressure
2. 2
   workup.ADDITIONpoured into 2N hydrochloric acid (200 ml)
3. 3
   Extraktionextracted with ethyl acetate (2×150 ml)
4. 4
   Extraktionextracted with ethyl acetate (2×150 ml)
5. 5
   TrocknenThe organic layers were dried over magnesium sulfate
6. 6
   Einengenconcentrated

Vorschrift

Triphenylphosphine (6.85 g) was added to a solution of 3-bromo-4-hydroxybenzaldehye (5 g) in tetrahydrofuran (40 ml), followed by addition of 2-hydroxyethylmorpholine (3.01 ml) and then the dropwise addition of diethylazodicarboxylate (4.11 ml). After 12 hours, the reaction was concentrated under reduced pressure, poured into 2N hydrochloric acid (200 ml) and extracted with ethyl acetate (2×150 ml). The aqueous layer was basified to pH 9 with solid sodium bicarbonate and extracted with ethyl acetate (2×150 ml). The organic layers were dried over magnesium sulfate and concentrated to afford 4.4 g (56%) of 4-morpholinoethoxy-3-bromobenzaldehyde as a reddish oil.

Quelle