Iodoethane → 7-Bromo-1-ethyl-1H-indole

HRID 2215757Notes

Reaction equation

HRID 2215757 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][CH:10]=[CH:9]2.I[CH2:14][CH3:15]>CN(C=O)C>[CH2:14]([N:11]1[C:12]2[C:8](=[CH:7][CH:6]=[CH:5][C:4]=2[Br:3])[CH:9]=[CH:10]1)[CH3:15]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 27570207-Bromoindole

Product 1

HCID 219500327-Bromo-1-ethyl-1H-indole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a 60% dispersion of sodium hydride in mineral oil (0.80 g, 21 mmol), suspended in DMF (50 mL), was added 7-bromoindole (2.0 g, 10 mmol) in DMF (15 mL) followed by a solution of iodoethane (1.64 mL, 26.3 mmol). After 20 minutes, the mixture was quenched with saturated NaHCO3, and poured into EtOAc. The organic layer which was separated, washed with saturated NaHCO3, dried (MgSO4) and concentrated to afford 1-ethyl-7-bromoindole as a brown oil which was used without further purification.

Workup

  1. customthe mixture was quenched with saturated NaHCO3
  2. additionpoured into EtOAc
  3. customThe organic layer which was separated
  4. washwashed with saturated NaHCO3
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9712799578c0460bbdfc717df6861f72
Source dataset
uspto-grants-2006_09
Patent number
US07109229B2

Reaction notes

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