Reaktion #607435

Reaktionsgleichung

(2Z)-(hydroxyimino)(phenyl)acetonitrile

2-bromo-4-(bromomethyl)thiazole

potassium iodide

caesium carbonate

→

(2Z)-{[(2-bromo-1,3-thiazol-4-yl)methoxy]imino}(phenyl)acetonitrile

Ausbeute 88.0%

Lösungsmittel

DMF

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent was then evaporated
2. 2
   workup.DISSOLUTIONthe residue dissolved in EtOAc
3. 3
   Waschensubsequently washed with H2O and brine
4. 4
   SonstigeAter separation
5. 5
   Trocknenthe organic phase was dried over MgSO4
6. 6
   Einengenthen concentrated
7. 7
   SonstigeThe residue was purified by chromatography on silica gel

Vorschrift

To a mixture of (2Z)-(hydroxyimino)(phenyl)acetonitrile (2.9 g, 19.84 mmol, 1 eq.), 2-bromo-4-(bromomethyl)thiazole (5.10 g, 19.84 mmol, 1 eq.), potassium iodide (329 mg, 1.98 mmol, 0.1 eq.) and caesium carbonate (9.70 g, 29.76 mmol, 1.5 eq.) was added 80 ml of acetonitrile and 10 ml of DMF. The reaction was stirred 2 h at room temperature. The solvent was then evaporated and the residue dissolved in EtOAc, subsequently washed with H2O and brine. Ater separation, the organic phase was dried over MgSO4 then concentrated. The residue was purified by chromatography on silica gel to give (2Z)-{[(2-bromo-1,3-thiazol-4-yl)methoxy]imino}(phenyl)acetonitrile (5.70 g, 88% yield, only 1 oxime isomer).

Quelle