Allyl bromide → 5-(prop-2-en-1-yloxy)-1H-indole

HRID 854504Notes

Reaction equation

HRID 854504 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.C([O-])([O-])=O.[K+].[K+].[CH2:17](Br)[CH:18]=[CH2:19]>CC(C)=O>[CH2:19]([O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2)[CH:18]=[CH2:17]

Participants

5

Reactant 3

HCID 7841Allyl bromide2×HCID 11430Potassium CarbonateHCID 160545-Hydroxyindole

Product 1

HCID 142392305-(prop-2-en-1-yloxy)-1H-indoleYield 81.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a slurry of 2.92 g (22 mmol) 5-hydroxyindole and 12.43 g (90 mmol) K2CO3 in 110 mL acetone was added 2.07 mL (24 mmol) allyl bromide. The reaction was stirred at room temperature over 2 days upon which time TLC indicated that the reaction was not complete. Additional 0.66 mL allyl bromide was added and the reaction was heated to reflux for 1.5 hr and stirred at room temperature over night. The reaction was filtered to remove precipitate and concentrated. The crude product was chromatographed on silica gel using 20–33% EtOAc-hexane to afford 3.128 g (18 mmol) 5-allyloxyindole as an oil.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 1.5 hr
  3. stirringstirred at room temperature over night
  4. filtrationThe reaction was filtered
  5. customto remove precipitate
  6. concentrationconcentrated
  7. customThe crude product was chromatographed on silica gel using 20–33% EtOAc-hexane

Sources & evidence

ORD record
ord-52a467e3f69d4757a136ed7545c3e791
Source dataset
uspto-grants-2007_08
Patent number
US07259182B2

Reaction notes

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