Methyl iodide → Methyl 4-bromo-3-(tetrahydropyran-2-yloxy)benzoate

HRID 1662339

Reaktionsgleichung

Reaktionsgleichung von HRID 1662339
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[O:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][O:13]1.Br[C:19]1C=CC(C(O)=O)=CC=1OC1CCCCO1.C(=O)([O-])[O-].[Cs+].[Cs+].IC>CC(C)=O.O>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:19])=[O:7])=[CH:4][C:3]=1[O:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][O:13]1

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 674295254-Bromo-3-(tetrahydro-2H-pyran-2-yloxy)benzoic acid 4-bromo-3-(tetrahydro-2H-pyran-2-yloxy)benzoic acid

Produkt 1

HCID 16747841Methyl 4-bromo-3-(tetrahydropyran-2-yloxy)benzoateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To flask containing 26.1 (2.15 g, 7.14 mmol) and cesium carbonate (3.95 g, 12.1 mmol) in acetone (50 mL), was added iodomethane (0.667 mL, 10.7 mmol). The resulting mixture was stirred overnight. The reaction was diluted with water and extracted with EtOAc. The organic layers were washed with brine, dried over Na2SO4, filtered, concentrated, and then purified by combiflash (0 to 20% EtOAc/Hexanes) to provide methyl 26.2 (2.25 g, 99% yield).

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washThe organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by combiflash (0 to 20% EtOAc/Hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-8bf91a6cce7a4ce999e9addf49610b4a
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08030354B2

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