Water → 6-Bromoindole-3-carbaldehyde

HRID 1618635Notes

Reaction equation

HRID 1618635 reaction equation
[Br:1][C:2]1[CH:10]=C2[C:5]([CH:6]=[CH:7]N2)=[CH:4][CH:3]=1.[CH3:11][N+:12]([CH3:15])=CCl.[Cl-].[OH2:17].[OH-].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:10]=[C:15]2[C:5]([C:6]([CH:7]=[O:17])=[CH:11][NH:12]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 77311Chloro-N,N-dimethylformiminium chlorideHCID 6764936-Bromoindole

Product 1

HCID 27948306-Bromoindole-3-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-bromo-1H-indole (4 g, 20.4 mmol) in DMF (20 mL) was added Vilsmeier reagent (3.929 g, 30.6 mmol) portion-wise and the resulting mixture was stirred at rt overnight. After 45 minutes, water (100 mL) was added and the mixture was stirred at rt overnight. Water (50 mL) and 10M aqueous NaOH (10 mL) was added and the reaction was stirred at rt until a precipitate formed. The resulting solid was filtered and dried under high vacuum to give 6-bromo-1H-indole-3-carbaldehyde and used as crude for the next step. Mass Spectrum (ESI) m/e=225 (M+1).

Workup

  1. waitAfter 45 minutes
  2. stirringthe mixture was stirred at rt overnight
  3. stirringthe reaction was stirred at rt until a precipitate
  4. customformed
  5. filtrationThe resulting solid was filtered
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-c93c7edbf5b04ede8f9ee88065920660
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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