Water → 1-Bromo-3-(1-methoxyethyl)benzene

HRID 334063Notes

Reaction equation

HRID 334063 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([CH:10]([OH:12])[CH3:11])[CH:7]=[CH:8][CH:9]=1.[CH3:13]I.O>CN(C=O)C>[Br:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([O:12][CH3:13])[CH3:11])[CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 984791-(3-Bromophenyl)ethanol

Product 1

HCID 685942561-Bromo-3-(1-methoxyethyl)benzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred and ice-cooled mixture of 1.09 g (27.4 mmol) NaH (60% in mineral oil) in 20 mL dry DMF was added a solution of 5.00 g (24.9 mmol) 1-(3-bromo-phenyl)-ethanol in 10 mL dry DMF under argon atmosphere. The mixture was stirred for 30 min at 0° C. 1.70 mL (27.4 mmol) methyl iodide was added and stirring was continued for 4 h at RT. The mixture was worked up by adding water, followed by extraction with EtOAc. The combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by flash chromatography (Cyc/EtOAc=9/1).

Workup

  1. temperatureice-cooled
  2. stirringThe mixture was stirred for 30 min at 0° C
  3. stirringstirring
  4. extractionfollowed by extraction with EtOAc
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude material was purified by flash chromatography (Cyc/EtOAc=9/1)

Sources & evidence

ORD record
ord-dc681b71c0d240e186108f56f463d81c
Source dataset
uspto-grants-2014_11
Patent number
US08883789B2

Reaction notes

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