Dimethylformamide → 5-Bromoindole-3-carbaldehyde

HRID 599500Notes

Reaction equation

HRID 599500 reaction equation
O=P(Cl)(Cl)Cl.[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([CH:21]=[O:22])C>>[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:21]=[O:22]

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 249055-Bromoindole

Product 1

HCID 701375-Bromoindole-3-carbaldehyde

Procedure

Dry DMF (7.5 ml) is cooled to 0° C. and treated dropwise with POCl3 (3.66 ml, 40 mmol). After stirring at this temperature for 15 min, a solution of 5-bromo-1H-indole (784 mg, 4 mmol) in dry DMF (2 ml) is added and the reaction mixture is allowed to warm to rt within 1 h. Stirring is continued at 40° C. for an additional hour, then the reaction mixture is cooled to rt and poured onto ice. Aqueous NaOH solution is added to neutralize the acidic solution, adjusting to pH 6. After stirring overnight at rt, the precipitate was collected by filtration, washed with water and dried under high vacuum to give pure subtitle compound (932 mg) as a beige solid in quantitative yield.

Workup

  1. stirringStirring
  2. waitis continued at 40° C. for an additional hour
  3. temperaturethe reaction mixture is cooled to rt
  4. additionpoured onto ice
  5. stirringAfter stirring overnight at rt
  6. filtrationthe precipitate was collected by filtration
  7. washwashed with water
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-03f265d37b4e42e5841b8a61f105b6f2
Source dataset
uspto-grants-2011_03
Patent number
US07897788B2

Reaction notes

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