Cesium carbonate → Methyl 3-(hydroxymethyl)-5-methylbenzoate

HRID 14103

Reaktionsgleichung

Reaktionsgleichung von HRID 14103
Br[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH2:12][OH:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[C:14](=O)([O-])[O-].[Cs+].[Cs+].C(=O)([O-])[O-].[K+].[K+].CB1OB(C)OB(C)O1>O1CCOCC1>[OH:13][CH2:12][C:10]1[CH:9]=[C:4]([CH:3]=[C:2]([CH3:14])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Komponenten

6

Edukt 4

HCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 11356988Methyl 3-bromo-5-(hydroxymethyl)benzoate

Produkt 1

HCID 21086184Methyl 3-(hydroxymethyl)-5-methylbenzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a stirred solution of methyl 3-bromo-5-(hydroxymethyl)benzoate (3.0 g, 12.2 mmol) in dioxane (27 mL) is added cesium carbonate (4.0 g, 12.2 mmol), potassium carbonate (34 g, 24.4 mmol), and palladium(0)tetrakis(triphenylphosphine) (704 mg, 0.61 mmol), followed by trimethyl boroxine (1.7 mL, 12.2 mmol). The reaction mixture is refluxed for 5 h, cooled to room temperature, and then partitioned between water and ethyl acetate. The organic layer is washed with water, saturated sodium bicarbonate, and brine, dried (magnesium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 20% ethyl acetate/hexanes) provides the title compound. ESI MS m/z 181.2 [M+H]+.

Aufarbeitung

  1. temperatureThe reaction mixture is refluxed for 5 h
  2. custompartitioned between water and ethyl acetate
  3. washThe organic layer is washed with water, saturated sodium bicarbonate, and brine
  4. dry with materialdried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by flash column chromatography (silica, 20% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-b2dd9ff51ddc4b6d97558449c6f3b845
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727997B2

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