Ammonium Chloride → 6-Bromo-4,4'-dimethyl-2,2'-bipyridyl

HRID 1159741Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1159741
Br[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([Br:9])[N:3]=1.[NH4+:10].[Cl-]>C1(C)C=CC=CC=1>[Br:9][C:4]1[N:3]=[C:2]([C:2]2[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:10]=2)[CH:7]=[C:6]([CH3:8])[CH:5]=1

Komponenten

4

Edukt 2

HCID 25517Ammonium ChlorideHCID 112881742,6-Dibromo-4-methylpyridine

Produkt 1

HCID 534387786-Bromo-4,4'-dimethyl-2,2'-bipyridylAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Dibromocompound 2,6-dibromo-4-methylpyridine (1 mmol), 2-tributylstannyl-picolines (1 mol) and (Ph3Ph)4Pd (0.01 equiv) were heated under N2 in toluene (50 mL) for 16 h. Upon cooling to room temperature aqueous saturated NH4Cl solution (20 mL) was added. The mixture was stirred for further 30 min and then filtered over Celite. The precipitate was washed with CH2Cl2 (50 mL) and the organic phase was separated. The aqueous phase was extracted with toluene. The combined organic phases were dried (MgSO4) and the solvent was removed. Concentrated HCl (30 mL) was added to the residue followed by extracting with CH2Cl2. The aqueous phase was cautiously neutralized by solid NaOH. The product was then extracted with CH2Cl2 and dried. The solvent was removed and the product purified by chromatography on silica gel with CH2Cl2/hexane (1:2) as eluent. Yield: 25%. Anal. C12H11BrN2: Calcd: C, 54.77; H, 4.21; N, 10.65. Found: C, 54.54; H, 4.30; N, 10.45. MS (ESIMS): m/z: 262.0.

Aufarbeitung

  1. additionwas added
  2. filtrationfiltered over Celite
  3. washThe precipitate was washed with CH2Cl2 (50 mL)
  4. customthe organic phase was separated
  5. extractionThe aqueous phase was extracted with toluene
  6. dry with materialThe combined organic phases were dried (MgSO4)
  7. customthe solvent was removed
  8. additionConcentrated HCl (30 mL) was added to the residue
  9. extractionby extracting with CH2Cl2
  10. extractionThe product was then extracted with CH2Cl2
  11. customdried
  12. customThe solvent was removed
  13. customthe product purified by chromatography on silica gel with CH2Cl2/hexane (1:2) as eluent

Quellen und Nachweise

ORD-Eintrag
ord-e092f473154444a39550144343a2a7ae
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07812251B2

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