Benzyl Bromide → HCID 53429317, compound

HRID 2177399Notes

Reaction equation

HRID 2177399 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:12].C(=O)([O-])[O-].[K+].[K+].[CH:19]1[CH:24]=[CH:23][C:22]([CH2:25]Br)=[CH:21][CH:20]=1>CC#N>[CH2:25]([O:11][C:8]1[CH:9]=[CH:10][C:2]([Br:1])=[C:3]2[C:7]=1[C:6](=[O:12])[CH2:5][CH2:4]2)[C:22]1[CH:23]=[CH:24][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 37180504-Bromo-7-hydroxy-1-indanone

Product 1

HCID 53429317HCID 53429317, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

Into a 250-mL round bottom flask, was placed 4-bromo-7-hydroxy-2,3-dihydro-1H-inden-1-one (1.5 g, 6.61 mmol, 1.00 equiv), CH3CN (30 mL) and potassium carbonate (1.83 g, 13.24 mmol, 2.00 equiv). BnBr (1.18 g, 6.90 mmol, 1.04 equiv) was added dropwise. The resulting solution was stirred for 2 h at 60° C. in an oil bath. The reaction progress was monitored by TLC (ethyl acetate/petroleum ether=1:4). The solids were removed by filtration. The resulting mixture was concentrated under reduced pressure. The residue was applied to a silica gel column, eluting with ethyl acetate/petroleum ether (1:4). This resulted in 2.1 g (95%) of 7-(benzyloxy)-4-bromo-2,3-dihydro-1H-inden-1-one as a yellow solid.

Workup

  1. customInto a 250-mL round bottom flask, was placed
  2. customThe solids were removed by filtration
  3. concentrationThe resulting mixture was concentrated under reduced pressure
  4. washeluting with ethyl acetate/petroleum ether (1:4)
  5. customThis resulted in 2.1 g (95%) of 7-(benzyloxy)-4-bromo-2,3-dihydro-1H-inden-1-one as a yellow solid

Sources & evidence

ORD record
ord-da1c9c2659ee41079cf63d4f22e96108
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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