Dimethylformamide → 4-Bromo-1H-indole-3-carbaldehyde

HRID 1159776Notes

Reaction equation

HRID 1159776 reaction equation
O=P(Cl)(Cl)Cl.[Br:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[CH:10][NH:11]2.CN([CH:19]=[O:20])C>>[Br:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[C:9]([CH:19]=[O:20])=[CH:10][NH:11]2

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 6764944-Bromoindole

Product 1

HCID 27631784-Bromo-1H-indole-3-carbaldehydeYield 65%

Conditions

Temperature
35 °C

Procedure

POCl3 (1.02 g, 6.63 mmol) was added dropwise to ice cold DMF (3 mL) and stirred for 15 min. 4-Bromoindole (1.00 g, 5.10 mmol) in DMF (1 mL) was added slowly. The mixture was heated to 35° C. with continuous stirring for 1.20 h (yellow precipitation was formed). The reaction mixture was cold on ice and treated with ice and 20% W/w aq. NaOH to pH 14 (pink color). Heating at reflux for 15 min. afforded a yellow clear solution, which formed a white precipitation when allowed to attain rt. The precipitation was filtered off, rinsed with ice cold water and dried under reduced pressure over weekend to give the title compound (1.14 g, 65%) as an off white solid. MS (ESI+) for C9H6BrNO m/z 224 (M+H)+.

Workup

  1. stirringwith continuous stirring for 1.20 h
  2. custom(yellow precipitation was formed)
  3. additiontreated with ice and 20% W/w aq. NaOH to pH 14 (pink color)
  4. temperatureHeating
  5. temperatureat reflux for 15 min.
  6. customafforded a yellow clear solution, which
  7. customformed
  8. customa white precipitation when
  9. customto attain rt
  10. customThe precipitation
  11. filtrationwas filtered off
  12. washrinsed with ice cold water
  13. customdried under reduced pressure over weekend

Sources & evidence

ORD record
ord-33dc0ab6685447529f8c0a43f8d33278
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

Loading…