Water → HCID 69342974, compound

HRID 855331Notes

Reaction equation

HRID 855331 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:11])([CH3:10])[CH3:9])=[C:4]([Cl:12])[CH:3]=1.[H-].[Na+].[CH3:15]I.O>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([O:11][CH3:15])([CH3:10])[CH3:9])=[C:4]([Cl:12])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58764285875307-00-9

Product 1

HCID 69342974HCID 69342974, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 370 mg (1.48 mmol) of 2-(4-bromo-2-chloro-phenyl)-propan-2-ol in 2 ml DMF was added to a suspension of sodium hydride (65 mg, ˜60% dispersion in oil) in 2 ml DMF at 0° C. The mixture was stirred at 0° C. for 30 min and then 111 μl (1.78 mmol) of methyl iodide were added. The reaction mixture was then warmed to rt and stirring was continued overnight. Then water was added and the mixture was extracted with ether. The organic phase was washed with water and brine, dried (MgSO4), filtered, and concentrated in vacuo to give a residue which was purified by flash column chromatography (1:9 ether/pentane). The title compound was obtained as a colorless liquid (310 mg, 79%). 1H NMR (CDCl3, 300 MHz): δ 1.64 (s, 6H), 3.13 (s, 3H), 7.35 (m, 2H), 7.54 (d, J=1.7 Hz, 1H).

Workup

  1. temperatureThe reaction mixture was then warmed to rt
  2. stirringstirring
  3. waitwas continued overnight
  4. extractionthe mixture was extracted with ether
  5. washThe organic phase was washed with water and brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give a residue which
  10. customwas purified by flash column chromatography (1:9 ether/pentane)

Sources & evidence

ORD record
ord-516c1d65e9ed4c79996295c81caa2832
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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