Lithium Hydroxide → 2-(4-Bromophenyl)cyclopropanecarboxylic acid

HRID 1294371

Reaktionsgleichung

Reaktionsgleichung von HRID 1294371
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:10][C@H:9]2[C:11]([O:13]C)=[O:12])=[CH:4][CH:3]=1.[Li+].[OH-]>C1COCC1.CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:10][CH:9]2[C:11]([OH:13])=[O:12])=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 69159174cis-Methyl 2-(4-bromophenyl)cyclopropanecarboxylate

Produkt 1

HCID 3015412-(4-Bromophenyl)cyclopropanecarboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21899815MeOH tetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of ester from step 2 in THF-MeOH (4:1, 0.5M) was added LiOH (3 eq, 2M) and the mixture was stirred at 50° C. for 1 h. The organic solvent was evaporated, the aqueous layer was acidified with HCl 1N and the acid extracted with EtOAc (3×). The combinedorganic extracts were washed with brine, dried and evaporated to afford 2-(4-bromophenyl)cyclopropanecarboxylic acid. Optically active intermediates were obtained by separation on chiral column (Chiral Pak AD) using hexane:EtOH (90:10 with 0.2% TFA).

Aufarbeitung

  1. customThe organic solvent was evaporated
  2. extractionthe acid extracted with EtOAc (3×)
  3. washThe combinedorganic extracts were washed with brine
  4. customdried
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-943a72b4c9e14438a1c327a66004231e
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07238706B2

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