1,4-Dibromobenzene → methyl (S)-3-(4-bromophenyl)-2-hydroxypropionate

HRID 910292

Reaktionsgleichung

Reaktionsgleichung von HRID 910292
C([Li])(C)(C)C.Br[C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][CH:8]=1.[Cu](C#N)C#N.[C:19]([O:24][CH3:25])(=[O:23])[C@H:20]1[O:22][CH2:21]1.[Cl-].[NH4+]>CCCCC>[Br:13][C:10]1[CH:11]=[CH:12][C:7]([CH2:21][C@H:20]([OH:22])[C:19]([O:24][CH3:25])=[O:23])=[CH:8][CH:9]=1

Komponenten

7

Edukt 5

HCID 78041,4-DibromobenzeneHCID 25517Ammonium ChlorideHCID 10942355Methyl (2S)-2-oxiranecarboxylateHCID 178418260HCID 178418260, VerbindungHCID 178418306HCID 178418306, Verbindung

Produkt 1

HCID 39359925methyl (S)-3-(4-bromophenyl)-2-hydroxypropionateAusbeute 133,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8003PentaneLösungsmittel

Reaktionsbedingungen

Temperatur
-30 °C

Versuchsvorschrift

100 ml (170 mmol) of a 1.7 M solution of tert-butyllithium in pentane are added dropwise to a solution of 48 g (204 mmol) of 1,4-dibromobenzene in 160 ml of tert-butyl dimethyl ether, cooled to −30° C., followed by addition of 7.3 g (82 mmol) of copper cyanide. The reaction medium is stirred for 15 minutes and a solution of 6 ml (68 mmol) of (S)-methyl glycidate in 10 ml of tert-butyl dimethyl ether is then added. After stirring for 20 minutes at −30° C., the reaction medium is hydrolysed with 150 ml of saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic phase is washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with heptane, and the polarity is then increased up to a 6/4 heptane/ethyl acetate mixture. 23.5 g (44%) of methyl 3-(4-bromophenyl)-2(S)-hydroxypropanoate are obtained.

Aufarbeitung

  1. stirringAfter stirring for 20 minutes at −30° C.
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue obtained
  8. customis purified by chromatography on a column of silica
  9. washeluted with heptane
  10. temperaturethe polarity is then increased up to a 6/4 heptane/ethyl acetate mixture

Quellen und Nachweise

ORD-Eintrag
ord-c044be1b64664c599a14b5eb357fd1ea
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022079B2

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