Реакция #1596943

Уравнение реакции

hydrochloric acid

1-benzyloxy-4-bromo-2-fluorobenzene

N-formylmorpholine

magnesium

→

4-benzyloxy-3-fluorobenzaldehyde

Растворители

MTBE

THF

THF

THF

THF

Условия реакции

Обработка

1. 1
   Температураa gentle reflux
2. 2
   Температураis maintained
3. 3
   Другоеafter initiation of the Grignard reaction
4. 4
   workup.ADDITIONWhen the addition
5. 5
   Температураthe batch is heated at the boil for 1 h
6. 6
   ДругоеThe organic phase is separated off
7. 7
   Экстракцияthe aqueous phase is extracted with MTBE
8. 8
   ПромывкаThe combined organic phases are washed with saturated sodium chloride solution
9. 9
   Другоеdried
10. 10
    КонцентрированиеThe solution is concentrated to dryness
11. 11
    Другоеthe crude product is recrystallised from n-heptane

Методика

25.9 g (1.07 mol) of magnesium turnings are initially introduced in 200 ml of THF, and a solution of 285.6 g (1.02 mol) of 1-benzyloxy-4-bromo-2-fluorobenzene in 700 ml of THF is added dropwise at such a rate that a gentle reflux is maintained after initiation of the Grignard reaction. When the addition is complete, the mixture is diluted with 1000 ml of THF, and the batch is heated at the boil for 1 h. The solution of the Grignard reagent is cooled to 0° C., and 118 ml (1.07 mol) of N-formylmorpholine in 100 ml of THF are added dropwise. After 1 h, the mixture is diluted with MTBE and hydrolysed using dilute hydrochloric acid. The organic phase is separated off, and the aqueous phase is extracted with MTBE. The combined organic phases are washed with saturated sodium chloride solution and dried using sodium sulfate. The solution is concentrated to dryness, and the crude product is recrystallised from n-heptane:MTBE.

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