Dimethylformamide → 6-Bromoindole-3-carbaldehyde

HRID 337611

Reaction equation

HRID 337611 reaction equation
CN([CH:4]=[O:5])C.[Br:6][C:7]1[CH:15]=[C:14]2[C:10]([CH:11]=[CH:12][NH:13]2)=[CH:9][CH:8]=1.P(Cl)(Cl)(Cl)=O.[OH-].[Na+]>O>[Br:6][C:7]1[CH:15]=[C:14]2[C:10]([C:11]([CH:4]=[O:5])=[CH:12][NH:13]2)=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 6764936-Bromoindole

Product 1

HCID 27948306-Bromoindole-3-carbaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a DMF (0.47 M) solution of 6-bromo-1H-indole (1 eq.) was added at 0° C. phosphorus oxychloride (1.2 eq.). The resulting solution was warmed to RT and stirred at RT for 16 h. The resulting solution was re-cooled to 0° C. and then carefully added NaOH (2 M aq. solution, 2.8 eq.). After stirring at RT for another 2 h, the crude reaction mixture was diluted with water and extracted with EtOAc. The combined organic extracts were dried over MgSO4. Filtration and concentration of the filtrate in vacuo afforded a yellow oil. Purification of the crude product thus obtained by way of flash chromatography (SiO2, Hex→EtOAc) afforded the title compound as a brown solid.

Workup

  1. temperatureThe resulting solution was re-cooled to 0° C.
  2. stirringAfter stirring at RT for another 2 h
  3. customthe crude reaction mixture
  4. extractionextracted with EtOAc
  5. dry with materialThe combined organic extracts were dried over MgSO4
  6. filtrationFiltration and concentration of the filtrate in vacuo
  7. customafforded a yellow oil
  8. customPurification of the crude product
  9. customthus obtained by way of flash chromatography (SiO2, Hex→EtOAc)

Sources & evidence

ORD record
ord-a0666ffeaddb423382df319d89bf3fe7
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Linked notes

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