4-Iodophenol → HCID 86698866, compound

HRID 338551Notes

Reaction equation

HRID 338551 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-b02e81145b0b4b27af7df85a5abc6e7c
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

Loading…