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

HRID 1656271Notes

Reaction equation

HRID 1656271 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 2× 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 2× 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-a3acf24cdd5340c4ad917f0d25f59d11
Source dataset
uspto-grants-1993_10
Patent number
US05252732

Reaction notes

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