Hydrogen Bromide → 5-(3-bromophenyl)pentanoic Acid

HRID 2402383

Reaktionsgleichung

Reaktionsgleichung von HRID 2402383
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])[CH:5]=[CH:6][CH:7]=1.Br.[H][H]>CCOC(C)=O.CC(O)=O.[Pd]>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])[CH:5]=[CH:6][CH:7]=1

Komponenten

7

Edukt 3

HCID 260Hydrogen BromideHCID 66728388HCID 66728388, VerbindungHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 116804435-(3-bromophenyl)pentanoic AcidAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 176Acetic AcidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 5-(3-Bromo-phenyl)-pent-4-enoic acid (4 g, 16 mmol) in EtOAc (150 mL) was added Pd/C (400 mg) and a solution of 40% HBr in AcOH (0.5 mL). The mixture was stirred at rt under 1 atm of hydrogen for 1 h. The reaction mixture was filtered and concentrated under reduced pressure. The crude material was purified by silica gel chromatography using a solvent system of 5:1 petroleum ether/EtOAc to give 5-(3-Bromo-phenyl)-pentanoic acid (3.2 g, 80%). 1H-NMR (400 MHz, CDCl3) δ ppm 7.3-7.4 (m, 2H), 7.05-7.15 (m, 2H), 2.55 (s, 2H), 2.35 (s, 2H), 1.7 (m, 4H).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. customThe crude material was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-28d6a8087d74424e8fedbcd3362840cb
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08796310B2

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