Benzyl Bromide → HCID 890054, compound

HRID 1009855Notes

Reaction equation

HRID 1009855 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([CH3:11])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Cl-].[NH4+]>[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].C(OCC)(=O)C.O.CN(C)C=O>[CH2:18]([O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([CH3:11])[CH:3]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

9

Reactant 4

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 701334-Hydroxy-2-methylacetophenone

Product 1

HCID 890054HCID 890054, compoundYield 105.1%

Reagents, catalysts & solvents 4

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To an N,N-dimethylformamide solution (20 mL) of 4′-hydroxy-2′-methylacetophenone (3.06 g, 20 mmol) were added potassium carbonate (3.66 g, 26.4 mmol), benzyl bromide (2.7 mL, 22.4 mmol), and n-Bu4NI (0.75 g, 2.03 mmol), and the mixture was stirred for 14 hours at room temperature. To the reaction solution cooled in ice were added a saturated solution of ammonium chloride, subsequently water and ethyl acetate to separate an organic layer. The organic layer was washed with 20% aqueous solution of sodium thiosulfate and brine, and dried with anhydrous magnesium sulfate. The drying agent was filtered off, and the solvent was evaporated under reduced pressure. Thus obtained residue was purified with silica gel column chromatography (hexane:ethyl acetate=8:1 to 6:1) to obtain the title compound (5.05 g, quant.) as a colorless powder.

Workup

  1. temperatureTo the reaction solution cooled in ice
  2. customto separate an organic layer
  3. washThe organic layer was washed with 20% aqueous solution of sodium thiosulfate and brine
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationThe drying agent was filtered off
  6. customthe solvent was evaporated under reduced pressure
  7. customThus obtained residue was purified with silica gel column chromatography (hexane:ethyl acetate=8:1 to 6:1)

Sources & evidence

ORD record
ord-4f25b8acea904e79ac169c88d5bc20b1
Source dataset
uspto-grants-2011_07
Patent number
US07973012B2

Reaction notes

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