Nonanoic Acid → Nonanoic acid, 2-bromo-

HRID 1742740Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1742740
[C:1]([OH:11])(=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[Br:12]Br.P(Cl)(Cl)Cl>C(OCC)(=O)C>[Br:12][CH:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])[C:1]([OH:11])=[O:10]

Komponenten

5

Edukt 3

HCID 8158Nonanoic AcidHCID 24387Phosphorus trichlorideHCID 24408Bromine

Produkt 1

HCID 102858Nonanoic acid, 2-bromo-Ausbeute 90,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of nonanoic acid (20 g, 126 mmol) and bromine (24.3 g 152 mmol) was added phosphorous trichloride (5.2 g, 38 mmol) slowly over 0.5 hour. The mixture was refluxed for 3 days and then diluted with ethyl acetate (200 mL). The organic phase was washed with aqueous saturated NaHSO3 (3×), separated, dried over anhydrous sodium sulfate, and the solvent removed in vacuo to yield 27.0 g of the title compound as a brown oil. 1H NMR (CDCl3, 60 MHz) δ0.70 (m, 3H), 1.20 (m, 9H), 1.90 (m, 3H), 4.13 (m, 1H), 10.80 (br s, 1H).

Aufarbeitung

  1. temperatureThe mixture was refluxed for 3 days
  2. washThe organic phase was washed with aqueous saturated NaHSO3 (3×)
  3. customseparated
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-940b2169fea84de2ac0f9c4a118c661b
Quelldatensatz
uspto-grants-1994_08
Patentnummer
US05340802

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