Phenol → 4-Bromo-2-chloro-1-(1-phenoxyethyl)benzene

HRID 1501273Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1501273
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:10])[CH3:9])=[C:4]([Cl:11])[CH:3]=1.[C:12]1(O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:10][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH3:9])=[C:4]([Cl:11])[CH:3]=1

Komponenten

6

Edukt 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 202581281-(4-Bromo-2-chlorophenyl)ethanol

Produkt 1

HCID 1185627374-Bromo-2-chloro-1-(1-phenoxyethyl)benzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 1-(4-bromo-2-chlorophenyl)ethanol (1.32 g, 5.6 mmol), phenol (525 mg, 5.6 mmol) and triphenylphosphine (2198 mg, 8.4 mmol) in tetrahydrofuran (30 mL) was stirred at room temperature for 0.5 hour. Diisopropyl azodicarboxylate (1695 mg, 8.4 mmol) was dropwise to the reaction mixture and was stirred at room temperature for 12 hours. The mixture was concentrated to give a residue. The residue was purified by column chromatography (silica gel, petroleum ethe/ethyl acetate=5:1) to give 4-bromo-2-chloro-1-(1-phenoxyethyl)benzene as a colorless oil (882 mg 54%).

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. customto give a residue
  3. customThe residue was purified by column chromatography (silica gel, petroleum ethe/ethyl acetate=5:1)

Quellen und Nachweise

ORD-Eintrag
ord-332dd4e13ffd47c88f39d1f35ed54d62
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09206128B2

Notizen zur Reaktion

Wird geladen…