Magnesium perchlorate → Methyl 2-bromo-2-(pyridin-2-yl)propanoate

HRID 2203306Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2203306
Cl([O-])(=O)(=O)=O.[Mg+2].Cl([O-])(=O)(=O)=O.[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH:18]([CH3:23])[C:19]([O:21][CH3:22])=[O:20].[Br:24]N1C(=O)CCC1=O>C(#N)C>[Br:24][C:18]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][N:12]=1)([CH3:23])[C:19]([O:21][CH3:22])=[O:20]

Komponenten

5

Edukt 3

HCID 24840Magnesium perchlorateHCID 67184N-bromobutanimideHCID 54595201Methyl 2-(pyridin-2-yl)propanoate

Produkt 1

HCID 67991933Methyl 2-bromo-2-(pyridin-2-yl)propanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Magnesium perchlorate (0.46 g, 2.08 mmol) was added to an acetonitrile (18 mL) solution containing the intermediate from Step A (1.04 g, 6.30 mmol). After stirring for 5 minutes N-bromosuccinimide (1.35 g, 7.55 mmol) was added and the reaction solution was stirred overnight. The solution was then partitioned between EtOAc and 1N NaHCO3 aq. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by silica gel chromatography using a hexanes/EtOAc gradient to give the indicated product. 1H NMR (400 MHz, CH3CN-d3): δ 8.48 (d, J=4.8 Hz, 1H); 7.85-736 (m, 2H); 7.32-7.26 (m, 1H); 3.72 (s, 3H); 2.24 (s, 3H). m/z=244.4 (M+H).

Aufarbeitung

  1. additionwas added
  2. customThe solution was then partitioned between EtOAc and 1N NaHCO3 aq. The organic layer
  3. washwas washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography
  8. customto give the indicated product

Quellen und Nachweise

ORD-Eintrag
ord-c89b665b907e4d389f7af17609d441c4
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09365574B2

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