Water → HCID 22482249, compound

HRID 1280446Notes

Reaction equation

HRID 1280446 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:16][CH:17]([Br:19])[CH3:18].O>CN(C=O)C>[Br:19][CH:17]([CH3:18])[CH2:16][O:8][C:5]1[CH:6]=[CH:7][C:2]([I:1])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 65531,2-DibromopropaneHCID 108944-IodophenolHCID 11430Potassium Carbonate

Product 1

HCID 22482249HCID 22482249, compoundYield 41.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a stirring solution of 4-iodophenol (15 g, 70 mmol) and K2CO3 (12.4 g, 90 mmol) in DMF (30 mL) was added 1,2-dibromopropane (7.8 mL, 90 mmol) over a period of 1 hr. The solution was heated at 50° C. and stirred overnight under Ar. Water (500 mL) was added and the reaction mixture was extracted with dichloromethane, dried over Na2SO4, filtered and the solvent evaporated under reduced pressure. Purified on silica gel chromatography, eluted with 10% ethyl acetate in hexanes to give the title compound as a white solid (10 g, 29 mmol).

Workup

  1. extractionthe reaction mixture was extracted with dichloromethane
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent evaporated under reduced pressure
  5. customPurified on silica gel chromatography
  6. washeluted with 10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-1404fd995284443f876b0910d11a3eb0
Source dataset
uspto-grants-2002_09
Patent number
US06451801B1

Reaction notes

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