Methyl iodide → 5-Bromo-1-methyl-1H-indole

HRID 1033493Notes

Reaction equation

HRID 1033493 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.[CH3:13]I>CS(C)=O.O>[CH3:13][N:9]1[C:10]2[C:6](=[CH:5][C:4]([Br:3])=[CH:12][CH:11]=2)[CH:7]=[CH:8]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 249055-Bromoindole

Product 1

HCID 2857575-Bromo-1-methyl-1H-indole

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A mixture of sodium hydroxide (0.4 g., 10 mmol.) in DMSO (20 mL.) was heated to 80°-85° C. for 6 hours to dissolve most of the solids then allowed to cool to room temperature. To the stirred mixture was added 5-bromoindole (2.0 g., 10 mmol.) followed in 1 hour by methyliodide (0.62 mL., 10 mmol.). After stirring for an additional 3 hours the reaction was shown by TLC analysis to be complete. The reaction mixture was diluted with water then extracted with ether. The extracts were washed 2x with water, dried with Na2SO4, and concentrated in vacuo to give 2.08 g. of 1-methyl-5-bromoindole as a yellow oil which crystallized on standing.

Workup

  1. temperaturewas heated to 80°-85° C. for 6 hours
  2. dissolutionto dissolve most of the solids
  3. extractionthen extracted with ether
  4. washThe extracts were washed 2x with water
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated in vacuo
  7. customto give 2.08 g
  8. customof 1-methyl-5-bromoindole as a yellow oil which crystallized

Sources & evidence

ORD record
ord-e049898b82624a68ab5326dbe066453a
Source dataset
uspto-grants-1994_05
Patent number
US05310901

Reaction notes

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