1-Iodo-4-[(2-methylbut-3-yn-2-yl)oxy]benzene → HCID 10913124, compound

HRID 1165195Notes

Reaction equation

HRID 1165195 reaction equation
[CH3:1][C:2]([O:6][C:7]1[CH:12]=[CH:11][C:10]([I:13])=[CH:9][CH:8]=1)([CH3:5])[C:3]#[CH:4]>N1C2C(=CC=CC=2)C=CC=1.CCOCC>[CH3:5][C:2]1([CH3:1])[CH:3]=[CH:4][C:8]2[CH:9]=[C:10]([I:13])[CH:11]=[CH:12][C:7]=2[O:6]1

Participants

4

Reactant 1

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

Product 1

HCID 10913124HCID 10913124, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 7047QuinolineSolvent

Procedure

A solution of 1-[(1,1-dimethyl-2-propynyl)oxy]-4-iodobenzene (5.97 g, 20.8 mmol) in quinoline (25 mL) was heated at 170° C. for 2 hours. The reaction was cooled to room temperature and diluted with ether. The reaction mixture was washed with 2N HCl (4X eq. vol.), with brine (2X eq. vol.), dried over anhydrous MgSO4 and concentrated to give crude product. This material was combined with product from an identical reaction and purified by flash chromatography, using 100% petroleum ether elution to give 5.58 g, (79% for the two reactions), of product.

Workup

  1. washThe reaction mixture was washed with 2N HCl (4X eq. vol.), with brine (2X eq. vol.)
  2. dry with materialdried over anhydrous MgSO4
  3. concentrationconcentrated
  4. customto give crude product
  5. customThis material was combined with product from an identical reaction
  6. custompurified by flash chromatography
  7. wash100% petroleum ether elution
  8. customto give 5.58 g

Sources & evidence

ORD record
ord-e496ebf3374341c9b30e48e82aa15b71
Source dataset
uspto-grants-1990_03
Patent number
US04908378

Reaction notes

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