2-Iodophenol → HCID 58488457, compound

HRID 2194869Notes

Reaction equation

HRID 2194869 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[CH3:9][O:10][CH2:11][CH2:12]Br.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.O>[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:12][CH2:11][O:10][CH3:9]

Participants

6

Reactant 3

HCID 107842-IodophenolHCID 10796Cesium carbonateHCID 809722-Bromoethyl methyl ether

Product 1

HCID 58488457HCID 58488457, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of commercially available 2-iodo phenol (1 eq.) and 2-bromoethyl methyl ether (1.1 eq) in DMF (0.21M) at 0° C. was added Cs2CO3 (1.5 eq). The mixture was stirred at 50° C. for 6 h, cooled to room temperature, poured in water and extracted with Et2O. The organic extract was washed with water, brine, dried over MgSO4 filtered and concentrated. Purification by column chromatography on silica gel, eluting with Hex/EtOAc 10%, afforded the desired compound as a colorless oil.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with Et2O
  3. extractionThe organic extract
  4. washwas washed with water, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by column chromatography on silica gel
  9. washeluting with Hex/EtOAc 10%

Sources & evidence

ORD record
ord-936171855ac147efb469896a456f76cd
Source dataset
uspto-grants-2012_12
Patent number
US08334308B2

Reaction notes

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