Phenol → HCID 69118208, Verbindung

HRID 1501056Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1501056
C(OC(N=NC(OC(C)C)=O)=O)(C)C.[Br:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22]([OH:25])[CH2:23][CH3:24])=[CH:18][CH:17]=1.[C:26]1(O)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[Br:15][C:16]1[CH:17]=[CH:18][C:19]([CH:22]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:23][CH3:24])=[CH:20][CH:21]=1

Komponenten

6

Edukt 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 1072904-Bromo-alpha-ethylbenzenemethanol

Produkt 1

HCID 69118208HCID 69118208, VerbindungAusbeute 73,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Azodicarboxylic acid diisopropyl ester (2.8 g, 14.0 mmol) was added to the mixture of 1-(4-bromophenyl)propan-1-ol (2.0 g, 9.3 mmol), phenol (1.05 g, 11.2 mmol), triphenylphosphine (3.7 g, 14.0 mmol) and tetrahydrofuran (40 mL) at room temperature. Then the mixture was stirred at room temperature for 12 hours. The resultant mixture was concentrated to give a residue. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=10:1) to give 1-bromo-4-(1-phenoxypropyl)benzene as a colorless oil (2.0 g, 4%). 1H NMR (300 MHz, CDCl3): δ 7.44 (d, J=8.4 Hz, 2H), 7.25-7.15 (m, 4H), 6.89-6.80 (m, 3H), 4.98 (t, J=6.5 Hz, 1H), 2.00-1.72 (m, 2H), 0.99 (t, J=7.5 Hz, 3H).

Aufarbeitung

  1. concentrationThe resultant mixture was concentrated
  2. customto give a residue
  3. customThe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-3ce5b5846d054b46965a804057bb8eb5
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09206128B2

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