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

HRID 1762160
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1762160
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 icewater (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 fraction 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. additionthe reaction mixture was poured into icewater (20 ml)
  2. extractionextracted with ethyl acetate (40 ml)
  3. washThe organic layer was washed with saturated aqueous sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. additionThe fraction containing the desired compound
  7. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0f25e3d4ee7844d3a117010f145249db
Quelldatensatz
uspto-grants-1989_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04831030

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