Phosphorus tribromide → HCID 86613513, compound

HRID 271027Notes

Reaction equation

HRID 271027 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[C:30]2[CH:29]=[CH:28][C:16]3[C:17](=[O:27])[N:18]([CH2:24][CH2:25]O)[C:19](=[O:23])[C:20]4=[CH:21][CH:22]=[C:13]([C:14]=2[C:15]=34)[C:12]1=[O:31])([CH3:4])([CH3:3])[CH3:2].P(Br)(Br)[Br:33]>C(Cl)(Cl)Cl>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[C:30]2[CH:29]=[CH:28][C:16]3[C:17](=[O:27])[N:18]([CH2:24][CH2:25][Br:33])[C:19](=[O:23])[C:20]4=[CH:21][CH:22]=[C:13]([C:14]=2[C:15]=34)[C:12]1=[O:31])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 86613514HCID 86613514, compound

Product 1

HCID 86613513HCID 86613513, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

0.92 g (2.22 mmol) of 1-(2-tert. butylphenyl)-6-(2-hydroxyethyl)-1H-indolo[5,4,3-def]isoquinoline-2,5,7(6H)-trione was dissolved in 60 mL of chloroform and heated to a boil. Then, 15 mL (15.54 mmol) of phosphorus tribromide was added dropwise within 20 minutes and the solution was heated at reflux for 2 hours. The reaction mixture was then poured onto ice, and the aqueous phase was extracted with chloroform. The combined organic phases were dried over magnesium sulfate. The purification was carried out by column chromatography on silica gel with toluene as the developing solvent.

Workup

  1. temperatureheated to a boil
  2. temperaturethe solution was heated
  3. temperatureat reflux for 2 hours
  4. additionThe reaction mixture was then poured onto ice
  5. extractionthe aqueous phase was extracted with chloroform
  6. dry with materialThe combined organic phases were dried over magnesium sulfate
  7. customThe purification

Sources & evidence

ORD record
ord-3f82b9299deb4e4aa0765f4c3fa12b68
Source dataset
uspto-grants-2008_11
Patent number
US07452385B2

Reaction notes

Loading…