Methyl iodide → 6-Bromo-1-methyl-1H-indole

HRID 381308Notes

Reaction equation

HRID 381308 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][NH:10]2)=[CH:6][CH:5]=1.I[CH3:14]>O1CCCC1>[Br:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][N:10]2[CH3:14])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 6764936-Bromoindole

Product 1

HCID 155468546-Bromo-1-methyl-1H-indoleYield 97.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (4.10 g of a 60% dispersion in paraffin wax) was added to a stirred solution of 6-bromoindole (10 g, 51.3 mmol) in tetrahydrofuran (100 ml) at 0° C. under a nitrogen atmosphere. After 1 hour iodomethane (6.38 ml. 102.6 mmol) was added and the cooling bath removed. After 12 hours methanol was added dropwise until effervescence ceased and then the solvent was removed in vacuo. The thick residue was diluted with dichloromethane and washed first with water then with brine. The organic layer was dried (magnesium sulphate) and concentrated in vacuo to give a dark yellow oil. Filtration through a plug of silica with 90% hexane/10% ethyl acetate as eluant gave the subtitle compound as a pale yellow oil (10.5 g).

Workup

  1. customthe cooling bath removed
  2. additionAfter 12 hours methanol was added dropwise until effervescence
  3. customthe solvent was removed in vacuo
  4. additionThe thick residue was diluted with dichloromethane
  5. washwashed first with water
  6. dry with materialThe organic layer was dried (magnesium sulphate)
  7. concentrationconcentrated in vacuo
  8. customto give a dark yellow oil
  9. filtrationFiltration through a plug of silica with 90% hexane/10% ethyl acetate as eluant

Sources & evidence

ORD record
ord-0fe7af1a3dda4f5fa1d13e2a3e2a12da
Source dataset
uspto-grants-2001_10
Patent number
US06306852B1

Reaction notes

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