Benzyl Bromide → HCID 890054, compound

HRID 2261790Notes

Reaction equation

HRID 2261790 reaction equation
O[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH3:11])=[O:4].[C:12](=[O:15])([O-])[O-].[Cs+].[Cs+].C(Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C=O)C>[CH2:12]([O:15][C:8]1[CH:9]=[CH:10][C:5]([C:3](=[O:4])[CH3:2])=[C:6]([CH3:11])[CH:7]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 213966992-Hydroxy-1-(2-methylphenyl)ethan-1-one

Product 1

HCID 890054HCID 890054, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Hydroxy-2′-methylacetophenone (5.508 g, 0.037 mol) in DMF (10 mL) is added cesium carbonate (23.8 g, 0.073 mol). The reaction is stirred at room temperature for 10 minutes. Benzyl bromide (4.36 mL, 0.037 mol) is added and after 1 hour at room temperature, the reaction is concentrated under reduced pressure. The residue is dissolved in ethyl acetate and water. The layers are separated and the organic phase is washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to give the title compound. ES/MS m/e 241.0 (M+1)

Workup

  1. concentrationthe reaction is concentrated under reduced pressure
  2. dissolutionThe residue is dissolved in ethyl acetate
  3. customThe layers are separated
  4. washthe organic phase is washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7c0d308bc499469fbbdffb97898ade0a
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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