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

HRID 363571

反応式

HRID 363571 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-266b27ef6048467da0c0aaa31a077117
出典データセット
uspto-grants-1999_02
特許番号
US05874435

関連ノート

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