반응 #1596943

반응 방정식

hydrochloric acid

1-benzyloxy-4-bromo-2-fluorobenzene

N-formylmorpholine

magnesium

→

4-benzyloxy-3-fluorobenzaldehyde

용매

MTBE

THF

THF

THF

THF

반응 조건

후처리

1. 1
   온도a gentle reflux
2. 2
   온도is maintained
3. 3
   기타after initiation of the Grignard reaction
4. 4
   workup.ADDITIONWhen the addition
5. 5
   온도the batch is heated at the boil for 1 h
6. 6
   기타The organic phase is separated off
7. 7
   추출the aqueous phase is extracted with MTBE
8. 8
   세척The combined organic phases are washed with saturated sodium chloride solution
9. 9
   기타dried
10. 10
    농축The solution is concentrated to dryness
11. 11
    기타the crude product is recrystallised from n-heptane

실험 절차

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.

출처