Potassium Carbonate → HCID 117843048, compound

HRID 2209299Notes

Reaction equation

HRID 2209299 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([I:9])=[C:6]([OH:8])[CH:7]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:17][C:18]([CH3:20])=[CH2:19]>CC(C)=O.CCOC(C)=O.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([I:9])=[C:6]([O:8][CH2:19][C:18]([CH3:20])=[CH2:17])[CH:7]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 3577853-Bromo-2-methyl-1-propeneHCID 66133335-chloro-2-iodophenol

Product 1

HCID 117843048HCID 117843048, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 5-chloro-2-iodophenol (1.21 g, 4.76 mmol) and K2CO3 (723 mg, 5.23 mmol) in acetone (20 mL) was added 3-bromo-2-methyl-propene (0.53 ml, 5.23 mmol), and the reaction was heated to reflux for 16 hours. The reaction was cooled, diluted with EtOAc and water, and the layers were separated. The aqueous layer was extracted with EtOAc (2×) and the combined organics were dried over MgSO4, filtered and concentrated to afford 4-chloro-1-iodo-2-((2-methylallyl)oxy)benzene which was used directly in the next step without further purification.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 16 hours
  3. temperatureThe reaction was cooled
  4. customthe layers were separated
  5. extractionThe aqueous layer was extracted with EtOAc (2×)
  6. dry with materialthe combined organics were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-e4211cc54b7e45c68bb9b2dfef13269c
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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