Phosphorus tribromide → 5-(1-Bromoethyl)-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine

HRID 4677

Reaktionsgleichung

Reaktionsgleichung von HRID 4677
O[CH:2]([C:4]1[C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=2)=[N:6][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:8][C:9]=1[CH3:10])[CH3:3].P(Br)(Br)[Br:27]>O1CCCC1>[Br:27][CH:2]([C:4]1[C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=2)=[N:6][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:8][C:9]=1[CH3:10])[CH3:3]

Komponenten

4

Edukt 2

HCID 24614Phosphorus tribromideHCID 201513975-(1-Hydroxyethyl)-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine

Produkt 1

HCID 201513945-(1-Bromoethyl)-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 5-(1-hydroxyethyl)-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine (1.8 g) in tetrahydrofuran (10 ml) was dropped to a solution of phosphorus tribromide (0.34 ml) in tetrahydrofuran (20 ml) under ice cooling. The reaction mixture was stirred for 5 hours at the same condition and poured into ice water and extracted with ethyl acetate. The organic layer was evaporated in vacuo. The residue was chromatographed on silicagel eluting with chloroform. The fractions containing the desired product were combined and evaporated in vacuo. The residue was crystallized from diisopropyl ether to afford 5-(1-bromoethyl)-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine (0.3 g).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. customThe organic layer was evaporated in vacuo
  3. customThe residue was chromatographed on silicagel
  4. washeluting with chloroform
  5. additionThe fractions containing the desired product
  6. customevaporated in vacuo
  7. customThe residue was crystallized from diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-d873a469a1aa4c19a659d20fa347bd64
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04727073

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