4-Iodophenol → HCID 86698866, compound

HRID 1054901Notes

Reaction equation

HRID 1054901 reaction equation
C(=O)([O-])[O-].[K+].[K+].[I:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.CS(O[CH:20]([CH3:42])[CH2:21][O:22][C:23]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=O)=O>O>[I:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH:20]([CH3:42])[CH2:21][O:22][C:23]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 108944-IodophenolHCID 11430Potassium CarbonateHCID 13777645HCID 13777645, compound

Product 1

HCID 86698866HCID 86698866, compoundYield 46.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of potassium carbonate (0.63 g, 4.5 mmol) in dimethylformaide (10 mL) was purged with nitrogen for 10 min at 75° C. 4-iodophenol (0.55 g, 2.5 mmol) was added to the mixture and the solution was purged with nitrogen for additional 10 min. To the reaction mixture 1-(trityloxy)propan-2-yl methanesulfonate (1.00 g, 2.53 mmol) was added and stirred for 24 hours at the same temperature. The reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate (20 mL*3). The combined organic layer was dried over sodium sulfate and concentrated. The crude product was purified by combiflash silica gel chromatography (petroleum ether:ethyl acetate=10:1) to give the title compound (600 mg, 46%) as colorless oil.

Workup

  1. customthe solution was purged with nitrogen for additional 10 min
  2. extractionextracted with ethyl acetate (20 mL*3)
  3. dry with materialThe combined organic layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe crude product was purified by combiflash silica gel chromatography (petroleum ether:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-38f3ae59f0264713981ea8121e38879f
Source dataset
uspto-grants-2016_07
Patent number
US09394285B2

Reaction notes

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