Ethyl Acrylate → ethyl (2E)-3-(6-bromo-5-methyl-3-pyridyl)acrylate

HRID 226357

Reaktionsgleichung

Reaktionsgleichung von HRID 226357
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5](I)=[CH:4][N:3]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(C(C)C)CC)(C)C.[C:41]([O:45][CH2:46][CH3:47])(=[O:44])[CH:42]=[CH2:43]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[Br:1][C:2]1[N:3]=[CH:4][C:5](/[CH:43]=[CH:42]/[C:41]([O:45][CH2:46][CH3:47])=[O:44])=[CH:6][C:7]=1[CH3:8]

Komponenten

8

Edukt 4

HCID 8821Ethyl AcrylateHCID 80271Tri-o-tolylphosphineHCID 81531DiisopropylethylamineHCID 101086802-Bromo-5-iodo-3-methylpyridine

Produkt 1

HCID 86603663ethyl (2E)-3-(6-bromo-5-methyl-3-pyridyl)acrylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 2-bromo-5-iodo-3-methylpyridine (1.5 g) in DMF (15 mL) was added palladium(II) acetate (56.5 mg) and tri-o-tolylphosphine (230 mg) and diisopropylethylamine (3.5 mL), and ethyl acrylate (1.09 mL). The mixture was heated at 90° C. for 1 hour. Resulting mixture was poured into water and extracted with AcOEt. The organic layer was washed with water and brine, and dried over Na2SO4, and the solvent was removed in vacuo. Residual brown oil was purified by silica gel column chromatography eluted with AcOEt and hexane (1:4-1:2) to give ethyl (2E)-3-(6-bromo-5-methyl-3-pyridyl)acrylate (1.00 g) as pale yellow powder.

Aufarbeitung

  1. customResulting mixture
  2. extractionextracted with AcOEt
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. customthe solvent was removed in vacuo
  6. customwas purified by silica gel column chromatography
  7. washeluted with AcOEt and hexane (1:4-1:2)

Quellen und Nachweise

ORD-Eintrag
ord-1526812b5b584f43bb9038b3b0fb20ce
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557127B2

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