Phosphorus tribromide → 2-Bromo-5-(2-bromoethyl)pyridine

HRID 1400904Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1400904
[Br:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH2:9]O)=[CH:4][CH:3]=1.P(Br)(Br)[Br:12]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][Br:12])=[CH:6][N:7]=1

Komponenten

4

Edukt 2

HCID 24614Phosphorus tribromideHCID 224732202-(6-Bromopyridin-3-yl)ethanol

Produkt 1

HCID 584744292-Bromo-5-(2-bromoethyl)pyridineAusbeute 87,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Alcohol 289 (1.75 g, 8.66 mmol) was treated with phosphorous tribromide (5.0 mL, 53 mmol) and the mixture was heated for 5 min, until the solid had melted and re-solidified. The mixture was cooled, treated with ice and partitioned between saturated aqueous sodium bicarbonate and dichloromethane. The organic phase was collected, washed with saturated aqueous sodium bicarbonate and brine, dried (anhydrous MgSO4), filtered and concentrated. Silica gel chromatography of the residue (eluent DCM) provided title compound 290 (2.0 g, 7.6 mmol, 87% yield) as a colorless solid. MS (M+H): 266.0

Aufarbeitung

  1. temperaturethe mixture was heated for 5 min, until the solid
  2. temperatureThe mixture was cooled
  3. additiontreated with ice
  4. custompartitioned between saturated aqueous sodium bicarbonate and dichloromethane
  5. customThe organic phase was collected
  6. washwashed with saturated aqueous sodium bicarbonate and brine
  7. dry with materialdried (anhydrous MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-13241e01ffea42919998fe0650decba0
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08906852B2

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