反応 #1596943

反応方程式

hydrochloric acid

1-benzyloxy-4-bromo-2-fluorobenzene

N-formylmorpholine

magnesium

→

4-benzyloxy-3-fluorobenzaldehyde

溶媒

MTBE

THF

THF

THF

THF

反応条件

後処理

1. 1
   温度a gentle reflux
2. 2
   温度is maintained
3. 3
   その他after initiation of the Grignard reaction
4. 4
   workup.ADDITIONWhen the addition
5. 5
   温度the batch is heated at the boil for 1 h
6. 6
   その他The organic phase is separated off
7. 7
   抽出the aqueous phase is extracted with MTBE
8. 8
   洗浄The combined organic phases are washed with saturated sodium chloride solution
9. 9
   その他dried
10. 10
    濃縮The solution is concentrated to dryness
11. 11
    その他the crude product is recrystallised from n-heptane

実験手順

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.

出典