Hydrogen Bromide → 5-Bromo-3-phenylpentan-1-ol

HRID 555592Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 555592
[C:1]1([CH:7]([CH2:11][CH2:12][OH:13])[CH2:8][CH2:9]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BrH:14]>C1(C)C=CC=CC=1>[Br:14][CH2:9][CH2:8][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:11][CH2:12][OH:13]

Komponenten

4

Edukt 2

HCID 260Hydrogen BromideHCID 134285463-Phenylpentane-1,5-diol

Produkt 1

HCID 669882615-Bromo-3-phenylpentan-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

3-Phenylpentane-1,5-diol (452 mg, 2.51 mmol) was dissolved in 48% aqueous hydrobromic acid (284 μL, 2.51 mmol) and toluene (2.5 mL), placed in a sealed tube, and heated in a microwave oven at 180° C. for 10 minutes. The mixture was cooled and purified by column chromatography on silica gel, eluting with 0-100% ethyl acetate/hexanes to give the title compound as a colorless oil. 1H NMR (500 MHz, CDCl3) δ 1.57 (br s, 1H), 1.81-1.97 (m, 2H), 2.08-2.23 (m, 2H), 2.97 (quintet, J=5.0 Hz, 1H), 3.06-3.14 (m, 1H), 3.24-3.31 (m, 1H), 3.42-3.49 (m, 1H), 3.49-3.56 (m, 1H), 7.17-7.25 (m, 3H), 7.28-7.33 (m, 2H).

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. custompurified by column chromatography on silica gel
  3. washeluting with 0-100% ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-f5680584667246d78c1354189d15ef8e
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08053455B2

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