Water → 6-Chloro-5-(trifluoromethyl)indole-3-carbaldehyde

HRID 1670741Notes

Reaction equation

HRID 1670741 reaction equation
P(Cl)(Cl)(Cl)=O.[Cl:6][C:7]1[CH:15]=[C:14]2[C:10]([CH:11]=[CH:12][NH:13]2)=[CH:9][C:8]=1[C:16]([F:19])([F:18])[F:17].O.[OH-].[Na+].CN(C)[CH:25]=[O:26]>>[Cl:6][C:7]1[CH:15]=[C:14]2[C:10]([C:11]([CH:25]=[O:26])=[CH:12][NH:13]2)=[CH:9][C:8]=1[C:16]([F:19])([F:17])[F:18]

Participants

6

Reactant 5

HCID 962WaterHCID 6228Dimethylformamide2×HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 231499126-chloro-5-(trifluoromethyl)-1H-indole

Product 1

HCID 860655846-Chloro-5-(trifluoromethyl)indole-3-carbaldehydeYield 89%

Conditions

Temperature
0 °C

Procedure

Phosphorus oxychloride (1.83 ml) was added dropwise to dimethylformamide (16 ml) under ice-cooling, and the mixture was stirred at 0° C. for 20 min. 6-Chloro-5-(trifluoromethyl)-1H-indole (3.24 g) dissolved in dimethylformamide (10 ml) was added to the reaction mixture, and the mixture was stirred at 0° C. for 3 hr. Water was added to the reaction mixture, and the mixture was stirred at room temperature for 3 hr, and the mixture was alkalified with a 1N aqueous sodium hydroxide solution. The precipitated solid was collected by filtration, washed with water and dried to give 6-chloro-5-(trifluoromethyl)indole-3-carbaldehyde (3.25 g, yield 89%).

Workup

  1. temperaturecooling
  2. additionwas added to the reaction mixture
  3. stirringthe mixture was stirred at 0° C. for 3 hr
  4. stirringthe mixture was stirred at room temperature for 3 hr
  5. filtrationThe precipitated solid was collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-00256fff5ac549af8e92053b6d94d293
Source dataset
uspto-grants-2011_08
Patent number
US07994196B2

Reaction notes

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