4-Iodophenol → 1-Iodo-4-[(2-methylbut-3-yn-2-yl)oxy]benzene

HRID 1165194ノート

反応式

HRID 1165194 の反応式
[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH3:15][C:16](Cl)([CH3:19])[C:17]#[CH:18]>CC#N>[CH3:15][C:16]([O:8][C:5]1[CH:6]=[CH:7][C:2]([I:1])=[CH:3][CH:4]=1)([CH3:19])[C:17]#[CH:18]

参加物

5

反応物 3

HCID 108944-IodophenolHCID 11430Potassium CarbonateHCID 706791-Butyne, 3-chloro-3-methyl-

生成物 1

HCID 149335571-Iodo-4-[(2-methylbut-3-yn-2-yl)oxy]benzene収率 93%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

To a solution of 4-iodophenol (5.01 g, 22.8 mmol) in CH3CN (100 mL) containing K2CO3 (15.7 g, 0.114 mol) was added KI (4.91 g, 29.6 mmol) followed by 3-methyl-3-chlorobutyne (7.01 g, 68.3 mmol) at room temperature. The reaction was heated to 80° C. for 60 hours. The reaction was cooled to room temperature, quenched with 2.5N NaOH and extracted with ether. The combined organic extracts were washed with 2.5N NaOH (2X eq. vol.), dried over anhydrous K2CO3 and concentrated. The residue was taken up in a minimal amount of 10% ether/petroleum ether and filtered through a 2" silica gel pad, using 10% ether/petroleum ether elution. The filtrate was concentrated to give 6.04 g, (93%) of product.

後処理

  1. additionwas added KI (4.91 g, 29.6 mmol)
  2. temperatureThe reaction was cooled to room temperature
  3. customquenched with 2.5N NaOH
  4. extractionextracted with ether
  5. washThe combined organic extracts were washed with 2.5N NaOH (2X eq. vol.)
  6. dry with materialdried over anhydrous K2CO3
  7. concentrationconcentrated
  8. filtrationfiltered through a 2" silica gel pad
  9. wash10% ether/petroleum ether elution
  10. concentrationThe filtrate was concentrated

出典と根拠

ORDレコード
ord-458c83f5b286416e8b6c079671227e87
出典データセット
uspto-grants-1990_03
特許番号
US04908378

反応ノート

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