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

HRID 264163ノート

反応式

HRID 264163 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[S:11][CH3:12].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:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[S:11][CH3:12]

参加物

5

反応物 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 30176621-(4-Hydroxy-3-(methylthio)phenyl)ethan-1-one

生成物 1

HCID 100406381-[4-(3-Bromopropoxy)-3-methylmercaptophenyl]ethanone

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A mixture of 1-[4-hydroxy-3-(methylmercapto)phenyl]-ethanone (5.4 g; 30 mmol), K2CO3 (4.2 g), 1,3-dibromopropane (8 g, 39 mmol) in acetonitrile (150 ml) was heated at reflux for 3 hours and stirred at room temperature overnight. Acetonitrile was removed at reduced pressure and the residue was extracted into dichloromethane (250 ml). Insolubles were filtered off. The dichloromethane solution was concentrated. The crude product was purified on a silica gel column (SiO2, 100 g; eluted with 3:2 hexane:dichloromethane, 1.6 l). The compound crystallized upon concentration, and the product (3.5 g, 39%) was recrystallized from ethanol (40 ml) to yield 1-[4-(3-bromopropoxy)-3-(methylmercapto)phenyl]ethanone as white needles, 2.0 g; m.p.=120°-122° C.

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. customAcetonitrile was removed at reduced pressure
  4. extractionthe residue was extracted into dichloromethane (250 ml)
  5. filtrationInsolubles were filtered off
  6. concentrationThe dichloromethane solution was concentrated
  7. customThe crude product was purified on a silica gel column (SiO2, 100 g; eluted with 3:2 hexane:dichloromethane, 1.6 l)
  8. customThe compound crystallized upon concentration
  9. customthe product (3.5 g, 39%) was recrystallized from ethanol (40 ml)

出典と根拠

ORDレコード
ord-96c0bf8e6f464f81966333b31317010d
出典データセット
uspto-grants-1997_07
特許番号
US05646161

反応ノート

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