Dimethylformamide → 5-Bromoindole-3-carbaldehyde

HRID 1403491Notes

Reaction equation

HRID 1403491 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(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 6228Dimethylformamide2×HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 249055-Bromoindole

Product 1

HCID 701375-Bromoindole-3-carbaldehydeYield 70%

Conditions

Temperature
17.5 °C

Procedure

To a solution of POCl3 (8.58 g, 55.96 mmol) in N,N-dimethylformamide (14.9 g, 203.9 mmol) was added a solution of 5-bromo-1H-indole (10.0 g, 51.0 mmol) in N,N-dimethylformamide (100 mL) dropwise at 0-10° C. The reaction mixture was stirred for 1 h at 0-35° C. and then poured into water/ice solution, adjusted the pH to 10 with aqueous sodium hydroxide and filtered to afford 5-bromo-1H-indole-3-carbaldehyde as a white solid (8.0 g, 70%).

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-e9b8927a9aea45d586426ed087ddc530
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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