Dimethyl Sulfate → 5-Bromo-2-chloro-4-methoxybenzonitrile

HRID 46228

Reaktionsgleichung

Reaktionsgleichung von HRID 46228
[Br:1][C:2]1[C:3]([OH:11])=[CH:4][C:5]([Cl:10])=[C:6]([CH:9]=1)[C:7]#[N:8].S(OC)(O[CH3:16])(=O)=O.O.[OH-].[Li+]>C1COCC1.CCOC(C)=O>[Br:1][C:2]1[C:3]([O:11][CH3:16])=[CH:4][C:5]([Cl:10])=[C:6]([CH:9]=1)[C:7]#[N:8]

Komponenten

6

Edukt 3

HCID 6497Dimethyl SulfateHCID 168937Lithium hydroxide, monohydrateHCID 533304525-Bromo-2-chloro-4-hydroxybenzonitrile2×

Produkt 1

HCID 672873335-Bromo-2-chloro-4-methoxybenzonitrileAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 5-bromo-2-chloro-4-hyroxybenzonitrile (compound 87, 38.1 g, 164 mmol), dimethyl sulfate (20.1 mL, 213 mmol), and lithium hydroxide monohydrate (8.93 g, 213 mmol) in THF (500 mL) was refluxed overnight. The mixture was cooled to ambient temperature and then diluted with EtOAc. The EtOAc solution was washed with water and brine prior to drying over anhydrous MgSO4. Filtration and removal of the voletiles under reduced pressure left the crude product which was purified by column chromatography (5-40% EtOAC/hexanes) to yield 5-bromo-2-chloro-4-methoxybenzonitrile (30.7 g, 76%) as a white solid.

Aufarbeitung

  1. temperaturewas refluxed overnight
  2. washThe EtOAc solution was washed with water and brine
  3. dry with materialto drying over anhydrous MgSO4
  4. filtrationFiltration and removal of the voletiles under reduced pressure
  5. waitleft the crude product which
  6. customwas purified by column chromatography (5-40% EtOAC/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-d8a489cf90a04a668a483a1680f139a3
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541380B2

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