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

HRID 1165194Notes

Reaction equation

HRID 1165194 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-458c83f5b286416e8b6c079671227e87
Source dataset
uspto-grants-1990_03
Patent number
US04908378

Reaction notes

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