Allyl iodide → 5-Bromo-1-(prop-2-en-1-yl)-1H-indole

HRID 1033496Notes

Reaction equation

HRID 1033496 reaction equation
[OH-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2.[CH2:13](I)[CH:14]=[CH2:15]>CS(C)=O.O>[CH2:15]([N:9]1[C:10]2[C:6](=[CH:5][C:4]([Br:3])=[CH:12][CH:11]=2)[CH:7]=[CH:8]1)[CH:14]=[CH2:13]

Participants

6

Reactant 3

HCID 11166Allyl iodideHCID 14798Sodium Hydroxide2×HCID 249055-Bromoindole

Product 1

HCID 189656835-Bromo-1-(prop-2-en-1-yl)-1H-indoleYield 60.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a stirred mixture of NaOH (204 mg., 5.1 mmol., 1 eq.) in DMSO (10 mL.) was added 5-bromoindole (1.0 g., 5.1 mmol., 1 eq.). The solution was stirred for three hours upon complete dissolution of the NaOH (approximately 1 h.). To this solution was added allyl iodide (0.466 mL., 5.1 mmol., 1 eq.) via syringe. After 2 h. the mixture was diluted with water and extracted 2×with diethyl ether. The organic extracts were combined, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The product was purified by flash column chromatography on silica gel (4:1 hexanes/acetone) affording 730 mg 1-allyl-5-bromoindole.

Workup

  1. extractionextracted 2×with diethyl ether
  2. dry with materialdried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe product was purified by flash column chromatography on silica gel (4:1 hexanes/acetone)

Sources & evidence

ORD record
ord-6e9df98a32a0481eb8280ac8a47b2d36
Source dataset
uspto-grants-1994_05
Patent number
US05310901

Reaction notes

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