1,3-Dibromopropane → 1-[4-(3-Bromopropoxy)-3,5-dibromophenyl]ethanone

HRID 357350

반응식

HRID 357350 반응식
[CH3:1][C:2]([C:4]1[CH:9]=[C:8]([Br:10])[C:7]([OH:11])=[C:6]([Br:12])[CH:5]=1)=[O:3].C([O-])([O-])=O.[K+].[K+].[Br:19][CH2:20][CH2:21][CH2:22]Br>C(#N)C>[Br:19][CH2:20][CH2:21][CH2:22][O:11][C:7]1[C:6]([Br:12])=[CH:5][C:4]([C:2](=[O:3])[CH3:1])=[CH:9][C:8]=1[Br:10]

참가 물질

5

반응물 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 761581-(3,5-Dibromo-4-hydroxyphenyl)ethan-1-one

생성물 1

HCID 219601181-[4-(3-Bromopropoxy)-3,5-dibromophenyl]ethanone

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A stirred mixture of 3,5-dibromo-4-hydroxyacetophenone (3.0 g, 10.1 mmol), K2CO3 (2.8 g, 20.3 mmol), 1,3-dibromo-propane (4.0 g, 19.8 mmol) in acetonitrile (100 ml) was heated at reflux for 5 hours. The solvent was removed. The crude product was extracted into dichloromethane (150 ml) and the insoluble inorganics were filtered off. The solution was concentrated to dryness again. Purification was carried out by flash chromatography on silica gel (45 g, SiO2 ; eluted with 1:1 hexane:dichloromethane). The material thus obtained (2.8 g) was recrystallized twice from isopropyl ether to give analytically pure 1-[4-(3-bromopropoxy)-3,5-dibromo-phenyl]ethanone, m.p.=87°-88° C.

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 5 hours
  3. customThe solvent was removed
  4. extractionThe crude product was extracted into dichloromethane (150 ml)
  5. filtrationthe insoluble inorganics were filtered off
  6. concentrationThe solution was concentrated to dryness again
  7. customPurification
  8. customThe material thus obtained (2.8 g)
  9. customwas recrystallized twice from isopropyl ether

출처 및 근거

ORD 기록
ord-43cce0293bcf47efa7a7a87e9f3b0b5f
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05840727

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