Carbon tetrabromide → Methyl 9-bromononanoate

HRID 649735

Reaktionsgleichung

Reaktionsgleichung von HRID 649735
[CH3:1][O:2][C:3](=[O:13])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]O.C(Br)(Br)(Br)[Br:15].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:13])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][Br:15]

Komponenten

5

Edukt 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 292983Nonanoic acid, 9-hydroxy-, methyl ester

Produkt 1

HCID 554142Methyl 9-bromononanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
4 °C

Versuchsvorschrift

A solution of methyl-9-hydroxy-nonanoate (1.1 g, 5.85 mmol, 1.0 equiv) in CH2Cl2 (30 mL, 0.2 M) at 0° C. was treated successively with CBr4 (2.5 g, 7.54 mmol, 1.3 equiv) and PPh3 (2.15 g, 8.19 mmol, 1.4 equiv) and the reaction mixture was stirred at 4° C. for 10 h. The reaction mixture was then concenctrated under reduced pressure and washed repeatedly with Et2O (8×10 mL washes). The Et2O washes were combined and concentrated under reduced pressure. Chromatography (SiO2,5 cm×15 cm, hexanes) afforded the intermediate as a clear, colorless oil (1.02 g, 1.47 g theorectical, 69.5 %): 1H NMR (CDCl3,250 MHz) d 3.64 (s, 3H, C(O)OCH3), 3.38 (t, 2H, J=6.8 Hz, CH2Br), 2.29 (t, 2H, J=7.4 Hz CH2C(O)OCH3), 1.83 (p, 2H, cH2CH2Br), 1.63 (m, 2H, CH2CH2C(O)OCH3) 1.47-1.28 (m, 8H, alkyl protons).

Aufarbeitung

  1. washwashed repeatedly with Et2O (8×10 mL washes)
  2. concentrationconcentrated under reduced pressure
  3. customChromatography (SiO2,5 cm×15 cm, hexanes) afforded the intermediate as a clear, colorless oil (1.02 g, 1.47 g theorectical, 69.5 %)

Quellen und Nachweise

ORD-Eintrag
ord-344b32fdaa57445e8956aa8a779ebe6e
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06271015B1

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