Water → 1-(2,4,6-Triiodophenoxy)-3-octyne

HRID 1728293Notes

Reaction equation

HRID 1728293 reaction equation
[CH:1]1[C:2]([I:10])=[CH:3][C:4]([I:9])=[C:5]([OH:8])[C:6]=1[I:7].C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][CH2:19][C:20]#[C:21][CH2:22][CH2:23][CH2:24][CH3:25].O>CN(C)C=O>[I:7][C:6]1[CH:1]=[C:2]([I:10])[CH:3]=[C:4]([I:9])[C:5]=1[O:8][CH2:18][CH2:19][C:20]#[C:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 118622,4,6-TriiodophenolHCID 124762061-Bromooct-3-yne

Product 1

HCID 153433351-(2,4,6-Triiodophenoxy)-3-octyneYield 32%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of triiodophenol (1.0 g, 2.1 mmol) and potassium carbonate (0.35 g, 2.54 mmol, 1.2 eq) in 4 ml of dimethylformamide was heated at 70° C. for 1 hr and then cooled to room temperature. 1-bromo-3-octyne was added in a single portion and the mixture was stirred for 1 hr. The reaction mixture was poured into water and the precipitated solids were collected by filtration. The collected solid was recrystallized from methanol to give 0.39 g (32%) of desired product. Mp 45° C.-49° C. Title Compound: 1H (300 MHz) and 13C (75 MHz) NMR spectra were consistent with the desired structure. Calculated for C14H15I3O: C, 28.99; H, 2.61; I, 65.64. Found: C, 28.92; H, 2.49; I, 65.67.

Workup

  1. temperaturecooled to room temperature
  2. filtrationthe precipitated solids were collected by filtration
  3. customThe collected solid was recrystallized from methanol

Sources & evidence

ORD record
ord-ac7fa8f0169c4ab993daf4a06a338758
Source dataset
uspto-grants-1994_07
Patent number
US05326553

Reaction notes

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