Реакция #607435

Уравнение реакции

(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

Выход 88.0%

Растворители

DMF

acetonitrile

Условия реакции

Обработка

1. 1
   ДругоеThe solvent was then evaporated
2. 2
   workup.DISSOLUTIONthe residue dissolved in EtOAc
3. 3
   Промывкаsubsequently washed with H2O and brine
4. 4
   ДругоеAter separation
5. 5
   Сушкаthe organic phase was dried over MgSO4
6. 6
   Концентрированиеthen concentrated
7. 7
   ДругоеThe residue was purified by chromatography on silica gel

Методика

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).

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