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Phosphorus oxybromide → 4-Bromo-1-(cyclopropylmethyl)pyridin-2(1H)-one

HRID 516616
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 516616
P(Br)(Br)([Br:3])=O.[CH:6]1([CH2:9][N:10]2[CH:15]=[CH:14][C:13](O)=[CH:12][C:11]2=[O:17])[CH2:8][CH2:7]1>CN(C=O)C>[Br:3][C:13]1[CH:14]=[CH:15][N:10]([CH2:9][CH:6]2[CH2:8][CH2:7]2)[C:11](=[O:17])[CH:12]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 24613Phosphorus oxybromideHCID 594970981-(Cyclopropylmethyl)-4-hydroxypyridin-2(1H)-one

Produkt 1

HCID 585545154-Bromo-1-(cyclopropylmethyl)pyridin-2(1H)-oneAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

Phosphorus oxybromide (5.4 g, 18.9 mmol) was added to a solution of intermediate D2 (1.42 g, 8.6 mmol) in DMF (140 ml) and the mixture was heated at 110° C. for 1 hour. After cooling in an ice bath the solution was partitioned between water and EtOAc. After three extractions with EtOAc, the combined organic fractions were dried (Na2SO4) and the solvent was evaporated in vacuo. The crude product was purified by column chromatography (silica gel; DCM as eluent). The desired fractions were collected and evaporated in vacuo to yield intermediate D3 (1.82 g, 93%).

Aufarbeitung

  1. temperatureAfter cooling in an ice bath the solution
  2. customwas partitioned between water and EtOAc
  3. extractionAfter three extractions with EtOAc
  4. dry with materialthe combined organic fractions were dried (Na2SO4)
  5. customthe solvent was evaporated in vacuo
  6. customThe crude product was purified by column chromatography (silica gel; DCM as eluent)
  7. customThe desired fractions were collected
  8. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-dda17fc7172146a29f8e759a77b2b6e2
Quelldatensatz
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09114138B2

Notizen zur Reaktion

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