반응 #57346

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1-Bromo-3-phenoxy-benzene

But-3-enyl-((S)-1-phenyl-ethyl)-amine

dibromobenzene

phenol

cesium carbonate

→

1-bromo-3-phenoxy-benzene

수율 53.0%

용매

NMP

반응 조건

후처리

1. 1
   여과The heterogeneous mixture is filtered through a bed of Celite
2. 2
   세척the residue is washed with EtOAc (1×20 mL)
3. 3
   workup.ADDITIONThe filtrate is diluted with 1N NaOH (200 mL)
4. 4
   추출extracted with EtOAc (3×100 mL)
5. 5
   건조dried over Na2SO4
6. 6
   여과filtered
7. 7
   농축concentrated under reduced pressures
8. 8
   기타to give crude product as a yellow oil which
9. 9
   기타is purified by column chromatography (100% hexanes)

실험 절차

1-Bromo-3-phenoxy-benzene (A) A mixture of dibromobenzene (3 g, 12.75 mmol), phenol (1 g, 10.6 mmol), copper(I) oxide (152 mgs, 1 mmol), and cesium carbonate (3.46 g, 10.6 mmol) in 8 mL of NMP is heated at 195° C. for 20 minutes in a microwave. The heterogeneous mixture is filtered through a bed of Celite and the residue is washed with EtOAc (1×20 mL). The filtrate is diluted with 1N NaOH (200 mL) and extracted with EtOAc (3×100 mL). The organics were combined, dried over Na2SO4, filtered and concentrated under reduced pressures to give crude product as a yellow oil which is purified by column chromatography (100% hexanes) to give 1-bromo-3-phenoxy-benzene as a colorless oil (1.4 g, 53%). LCMS m/z 250 (M+1).

출처