Tetrahydrofuran → 6-Bromo-1-methyl-1H-indole

HRID 651743Notes

Reaction equation

HRID 651743 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[H-].[Na+].[CH2:13]1COCC1>>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[CH3:13])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 6764936-Bromoindole

Product 1

HCID 155468546-Bromo-1-methyl-1H-indoleYield 97%

Procedure

6-Bromoindole (10.4 g, 53.1 mmol) (prepared according to Moyer, M. P.; Shiurba, J. F.; Rapoport, H. J. Org. Chem. 1986, 51, 5106.) was added in small portions over 30 min to a stirred suspension of sodium hydride (2.96 g, 61.7 mmol, 50% in mineral oil) in dry THF (120 mL) at 0° C. Stirring was continued for another 30 min. lodomethane (4.5 ml, 71.6 mmol) was added dropwise. After 1 h, the mixture was poured into ice-water and extracted with ether (3×200 mL). The combined organic extracts were washed with brine and dried (MgSO4). Evaporation of the solvents and chromatography of the residue over silica gel using hexane gave 6-bromo-1-methyl-1H-indole (10.8 g, 97%).

Workup

  1. additionlodomethane (4.5 ml, 71.6 mmol) was added dropwise
  2. waitAfter 1 h
  3. extractionextracted with ether (3×200 mL)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. customEvaporation of the solvents and chromatography of the residue over silica gel

Sources & evidence

ORD record
ord-824b5ebefcaa4e5c8b0cc932b3558c29
Source dataset
uspto-grants-2001_08
Patent number
US06281356B1

Reaction notes

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