Water → 6-Bromoindole-3-carbaldehyde

HRID 1399861

Reaction equation

HRID 1399861 reaction equation
O=P(Cl)(Cl)Cl.[Br:6][C:7]1[CH:15]=[C:14]2[C:10]([CH:11]=[CH:12][NH:13]2)=[CH:9][CH:8]=1.O.[OH-].[Na+].CN([CH:22]=[O:23])C>>[Br:6][C:7]1[CH:15]=[C:14]2[C:10]([C:11]([CH:22]=[O:23])=[CH:12][NH:13]2)=[CH:9][CH:8]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6228Dimethylformamide2×HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 6764936-Bromoindole

Product 1

HCID 27948306-Bromoindole-3-carbaldehyde

Procedure

POCl3 (980 mg, 6.4 mmol) was added dropwise to DMF (3 mL) cooled in an ice bath. The mixture was stirred at 0° C. for 30 min before a solution of 6-bromo-1H-indole (1.0 g, 5.1 mmol) in DMF (7 mL) was slowly added at 0° C. The mixture was stirred at room temperature for 3 h before being poured into water and neutralized with 1N NaOH. The crude product was collected by filtration and used in next step without further purification. LCMS (m/z): 224.1 [M+H]+.

Workup

  1. temperaturecooled in an ice bath
  2. additionwas slowly added at 0° C
  3. filtrationThe crude product was collected by filtration
  4. customused in next step without further purification

Sources & evidence

ORD record
ord-b11a318bb24540bbb61be046c7947240
Source dataset
uspto-grants-2014_12
Patent number
US08906900B2

Linked notes

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