Hydrochloric Acid → 5-Bromo-1-methyl-1H-indole

HRID 1593999Notes

Reaction equation

HRID 1593999 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[OH-].[K+].I[CH3:14].Cl>CS(C)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:14])[CH:6]=[CH:5]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 249055-Bromoindole

Product 1

HCID 2857575-Bromo-1-methyl-1H-indoleYield 94%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

980 mg (5.0 mmol) of 5-bromoindole were added to a solution of 420 mg (7.5 mmol) of pulverized KOH in dimethyl sulfoxide (15 ml) following stirring 15 min at RT. After stirring at RT a further 5 min, 342 μl (5.5 mmol) of iodomethane were added and the mixture was then stirred at RT over a period of 1 h. Following neutralization with 5% strength aq. hydrochloric acid, the reaction mixture was extracted with EA. The organic phase was successively washed with water and a satd aq. NaCl soln and dried over MgSO4. Following filtration and removal of the solvent in vacuo there were obtained 980 mg (4.7 mmol, 93%) of 5-bromo-1-methylindole.

Workup

  1. stirringAfter stirring at RT a further 5 min
  2. stirringthe mixture was then stirred at RT over a period of 1 h
  3. extractionthe reaction mixture was extracted with EA
  4. washThe organic phase was successively washed with water
  5. dry with materiala satd aq. NaCl soln and dried over MgSO4
  6. filtrationfiltration and removal of the solvent in vacuo

Sources & evidence

ORD record
ord-152578ffeb5b4c619ff4ea6cc6ef005f
Source dataset
uspto-grants-2007_11
Patent number
US07300939B2

Reaction notes

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