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Potassium Carbonate → 3-Bromomethyl-2-methyl-4-(3-nitrophenyl)-6-phenylpyridine

HRID 2106823
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2106823
P(Br)(Br)[Br:2].O[CH2:6][C:7]1[C:8]([CH3:28])=[N:9][C:10]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:11][C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[Br:2][CH2:6][C:7]1[C:8]([CH3:28])=[N:9][C:10]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:11][C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 24614Phosphorus tribromideHCID 104712403-Hydroxymethyl-2-methyl-4-(3-nitrophenyl)-6-phenylpyridine

Produkt 1

HCID 100913483-Bromomethyl-2-methyl-4-(3-nitrophenyl)-6-phenylpyridineAusbeute 37,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028Tetrahydrofuran
Lösungsmittel
2×

Versuchsvorschrift

To a solution of phosphorus tribromide (0.93 g) in tetrahydrofuran (10 ml) was dropwise added a suspension of 3-hydroxymethyl-2-methyl-4-(3-nitrophenyl)-6-phenylpyridine (1.65 g) in tetrahydrofuran (10 ml) at 5°-10° C. After stirring for 1.5 hours at the same temperature, the reaction mixture was poured into ice-water (20 ml), adjusted to pH 9.5 with saturated aqueous potassium carbonate and extracted with ethyl acetate (40 ml). The organic layer was washed with saturated aqueous sodium chloride, dried over magnesium sulfate and evaporated in vacuo. The residue was subjected to a column chromatography on silica gel eluting with chloroform. The fractions containing the desired compound were combined and evaporated in vacuo to give 3-bromomethyl-2-methyl-4-(3-nitrophenyl)-6-phenylpyridine (0.49 g).

Aufarbeitung

  1. extractionextracted with ethyl acetate (40 ml)
  2. washThe organic layer was washed with saturated aqueous sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. additionThe fractions containing the desired compound
  6. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6938f60d7696403b97c5ff6265e2d3c4
Quelldatensatz
uspto-grants-1990_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04931453

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