N-bromobutanimide → Ethyl 2-(bromomethyl)pyridine-3-carboxylate

HRID 2202577

Reaktionsgleichung

Reaktionsgleichung von HRID 2202577
[CH3:1][C:2]1[N:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[Br:13]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:13][CH2:1][C:2]1[N:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 74401Ethyl 2-methylnicotinate

Produkt 1

HCID 825758Ethyl 2-(bromomethyl)pyridine-3-carboxylateAusbeute 59,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

Under a nitrogen atmosphere, ethyl 2-methylnicotinate (1.65 g, 10 mmol) was dissolved in carbon tetrachloride, and N-bromosuccinimide (2.31 g, 13 mmol) and azoisobutyronitrile (164 mg, 1 mmol) were added thereto. The mixture was refluxed for 8 hours. After the completion of the reaction was confirmed by HPLC, the reaction mixture was allowed to cool down to a room temperature. The organic layer was washed with water 3 times and then with a saturated saline solution, and dried over magnesium sulfate. After the solvent was distilled off, the resulting residue was purified by flash column chromatography (Yamazen, Hi-Flash column, silica gel, hexane/ethyl acetate (volume ratio)=10:1) to give the title compound (1.45 g, 59.4%) as an oily substance.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 8 hours
  2. washThe organic layer was washed with water 3 times
  3. dry with materialwith a saturated saline solution, and dried over magnesium sulfate
  4. distillationAfter the solvent was distilled off
  5. customthe resulting residue was purified by flash column chromatography (Yamazen, Hi-Flash column, silica gel, hexane/ethyl acetate (volume ratio)=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-ce174639d0ae4f24888c9eeab2b6f732
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09365553B2

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