Iodine → 1-Chloro-7-iodoisoquinoline

HRID 1896882Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1896882
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2[Cl:12])=[CH:4][CH:3]=1.[Li]CCCC.[I:18]I.[O-]S([O-])(=S)=O.[Na+].[Na+]>C1COCC1>[Cl:12][C:9]1[C:10]2[C:5](=[CH:4][CH:3]=[C:2]([I:18])[CH:11]=2)[CH:6]=[CH:7][N:8]=1

Komponenten

6

Edukt 4

HCID 807IodineHCID 24477Sodium ThiosulfateHCID 65020247-Bromo-1-ChloroisoquinolineHCID 178418339Butyllithium

Produkt 1

HCID 441563091-Chloro-7-iodoisoquinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 7-bromo-1-chloroisoquinoline (15 g, 62 mmol) in THF at −78° C., n-BuLi (123.7 mmol) was added. The resulting solution was stirred for 15 min. and, I2 (31.4 mg, 123.7 mmol) in THF was slowly added by syringe over a period of 5 min. The solution was then allowed to reach room temperature and treated with a saturated aqueous Na2S2O3 solution. The resulting mixture was extracted with diethyl ether (2×). The extracted organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuum. The residue was purified by flash chromatography to give the title compound.

Aufarbeitung

  1. customto reach room temperature
  2. extractionThe resulting mixture was extracted with diethyl ether (2×)
  3. washThe extracted organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuum
  6. customThe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8693a4490e4447dea79b5db62924f505
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08518969B2

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