Dimethylformamide → 5-Bromoindole-3-carbaldehyde

HRID 375983Notes

Reaction equation

HRID 375983 reaction equation
P(Cl)(Cl)(Cl)=O.[Br:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[CH:10]2.[OH-].[Na+].CN(C)[CH:20]=[O:21]>>[Br:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[C:10]2[CH:20]=[O:21]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 249055-Bromoindole

Product 1

HCID 701375-Bromoindole-3-carbaldehydeYield 97.7%

Conditions

Temperature
10 °C

Procedure

To a solution of phosphorous oxychloride (26.1 g) and dry dimethylformamide (50.9 ml), cooled to -10° C., was added 5-bromoindole (30 g) in portions. The reaction mixture was stirred at 10° C. for 1 hr. and at 35° C. for 1 hr. Ice (100 g) was added to the reaction mixture, followed by sodium hydroxide solution (50 ml). The mixture was heated on a steam bath for one-half hour. The precipitate was collected and recrystallized from ethanol to give 35.5 g (97.7%) of product.

Workup

  1. waitand at 35° C. for 1 hr
  2. temperatureThe mixture was heated on a steam bath for one-half hour
  3. customThe precipitate was collected
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-5a0086fd44cf47c98a614a574ce88797
Source dataset
uspto-grants-1996_01
Patent number
US05488063

Reaction notes

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