2-Ethyl-1-butanol → 1-Bromo-3-(2-ethylbutoxy)benzene

HRID 875530

Reaktionsgleichung

Reaktionsgleichung von HRID 875530
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[CH2:9]([CH:11]([CH2:14][CH3:15])[CH2:12]O)[CH3:10]>>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:12][CH:11]([CH2:14][CH3:15])[CH2:9][CH3:10])[CH:3]=1

Komponenten

3

Edukt 2

HCID 73582-Ethyl-1-butanolHCID 115633-Bromophenol

Produkt 1

HCID 673177401-Bromo-3-(2-ethylbutoxy)benzene

Versuchsvorschrift

Coupling of 3-bromophenol (17) (5.0 g, 28.9 mmol) with 2-ethylbutan-1-ol (3.25 g, 31.79 mmol) was conducted following the procedure given for Example 6. The reaction mixture was concentrated under reduced pressure then triturated with diethyl ether. The suspension was filtered and the filtrate was concentrated under reduced pressure. Purification by flash chromatography (100% hexanes) gave 1-bromo-3-(2-ethylbutoxy)benzene a clear liquid. Yield (5.04 g, 62%): 1H NMR (400 MHz, DMSO-d6) δ 7.20 (t, J=8.0 Hz, 1H), 7.11 (t, J=2.2 Hz, 1H), 7.07 (dd, J=8.0, 2.0 Hz, 1H), 6.92 (dd, J=8.4, 2.6 Hz, 1H), 3.84 (d, J=5.6 Hz, 2H), 1.61-1.53 (m, 1H), 1.46-1.30 (m, 4H), 0.86 (t, J=7.4 Hz, 6H).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthen triturated with diethyl ether
  3. filtrationThe suspension was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customPurification by flash chromatography (100% hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-2f71717abc794c0db2aa3950fd35ae8d
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08981153B2

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