Water → 5-Bromo-3-(2-methoxyethyl)benzo[d]oxazol-2(3H)-one

HRID 216958

Reaktionsgleichung

Reaktionsgleichung von HRID 216958
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](=[O:10])[NH:7][C:6]=2[CH:11]=1.Br[CH2:13][CH2:14][O:15][CH3:16].C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](=[O:10])[N:7]([CH2:13][CH2:14][O:15][CH3:16])[C:6]=2[CH:11]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 268532-Benzoxazolinone, 5-bromo-HCID 809722-Bromoethyl methyl ether

Produkt 1

HCID 579996905-Bromo-3-(2-methoxyethyl)benzo[d]oxazol-2(3H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 5-bromobenzo[d]oxazol-2(3H)-one (2.06 g), 1-bromo-2-methoxyethane (1.085 mL) and potassium carbonate (3.99 g) in acetonitrile (15 mL) was heated at 60° C. for 16 h. Water was added and the mixture was extracted with ethyl acetate (3 times). The organic layers were dried over magnesium sulfate, evaporated and purified by flash silica chromatography eluting with 5:1 isohexane/acetone to give the subtitled compound (1.359 g).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate (3 times)
  2. dry with materialThe organic layers were dried over magnesium sulfate
  3. customevaporated
  4. custompurified by flash silica chromatography
  5. washeluting with 5:1 isohexane/acetone

Quellen und Nachweise

ORD-Eintrag
ord-3cbfe3c24c8f4346a5aba6ed41fa7788
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193239B2

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