Methyl iodide → 2-Bromophenethyl methyl ether

HRID 2194868Notes

Reaction equation

HRID 2194868 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][OH:10].[H-].[Na+].I[CH3:14]>C1COCC1.CN(C=O)C.[NH4+].[Cl-]>[CH3:14][O:10][CH2:9][CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Br:1]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 27340892-(2-Bromophenyl)ethan-1-ol

Product 1

HCID 51519972-Bromophenethyl methyl ether

Reagents, catalysts & solvents 2

HCID 25517Ammonium ChlorideSolventHCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

To a solution of commercially available 2-(2-bromophenyl)ethanol (1 eq.) in THF/DMF (4/1; 0.12M) at 0° C. was added NaH (60% dispersion in oil; 1.5 eq). The mixture was stirred for 30 min then iodomethane (2 eq.) was added. The final mixture was stirred for 12 h at room temperature, poured in saturated aqueous NH4Cl and then extracted with Et2O. The organic extract was washed with water, brine, dried over MgSO4 filtered and concentrated. Purification by column chromatography on silica gel (Combi Flash from ISCO), eluting with Hex/EtOAc 0 to 50%, afforded the desired compound as a colorless oil.

Workup

  1. extractionextracted with Et2O
  2. extractionThe organic extract
  3. washwas washed with water, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by column chromatography on silica gel (Combi Flash from ISCO)
  8. washeluting with Hex/EtOAc 0 to 50%

Sources & evidence

ORD record
ord-9bb2632a967b4112a6160a926c919523
Source dataset
uspto-grants-2012_12
Patent number
US08334308B2

Reaction notes

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