Benzyl Bromide → 6-(Benzyloxy)-2,3-dihydro-1H-inden-1-one

HRID 2098957Notes

Reaction equation

HRID 2098957 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.Br[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O>[CH2:13]([O:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 70206596-Hydroxy-1-indanone

Product 1

HCID 224199626-(Benzyloxy)-2,3-dihydro-1H-inden-1-oneYield 67%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 6-hydroxy-2,3-dihydroinden-1-one (available from Aldrich) (5.0 g, 34 mmol), 1-(bromomethyl)benzene (1.1) (available from Aldrich) (4.4 mL, 37 mmol) and cesium carbonate (25 g, 78 mmol) in DMF were stirred at room temperature for 23 hours. The reaction mixture was diluted with EtOAc (400 mL). The mixture was washed with brine and dried over anhydrous sodium sulfate. After removing solvent by rotary evaporation, the residue was purified by column chromatography (1:4 EtOAc/hexane). Product 1.2 was obtained in 67% yield as a white solid.

Workup

  1. washThe mixture was washed with brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customAfter removing solvent
  4. customby rotary evaporation
  5. customthe residue was purified by column chromatography (1:4 EtOAc/hexane)

Sources & evidence

ORD record
ord-626a847ff7244bd6b0c6c74c3dfbbd68
Source dataset
uspto-grants-2013_05
Patent number
US08450522B2

Reaction notes

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