Triethylamine → 4-Bromo-2-methoxy-1-phenoxy-benzene

HRID 51571

Reaktionsgleichung

Reaktionsgleichung von HRID 51571
[Br:1][C:2]1[CH:3]=[C:4]([OH:10])[C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.[C:11]1(B(O)O)[CH:16]=[CH:15]C=[CH:13][CH:12]=1.[CH2:20](N(CC)CC)C>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:15]=[CH:16][CH:11]=[CH:12][CH:13]=2)=[C:4]([O:10][CH3:20])[CH:3]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 1422285-Bromo-2-methoxyphenol

Produkt 1

HCID 227362824-Bromo-2-methoxy-1-phenoxy-benzeneAusbeute 12 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8895Cupric acetateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 4-bromoguaiacol (2.23 g, 11 mmol), phenyl boronic acid (4.03 g, 33 mmol), copper(II) acetate (2.18 g, 12 mmol) and 4A powdered molecular sieves (20 g) in dichloromethane (100 mL) was treated with triethylamine (5.5 g, 55 mmol) then stirred at ambient temperature for 20 hours. The mixture was filtered, concentrated under reduced pressure and purified by flash chromatography on silica gel using heptane/ethyl acetate (75:25) as an eluent to give 4-bromo-2-methoxy-1-phenoxybenzene (350 mg, 12%): 1H NMR (DMSO-d6, 400 MHz) δ 7.3-7.4(m, 3H), 7.15(d, 1H), 7.05(t, 1H), 6.98(d, 1H), 6.85 (d, 2H), 3.77(s, 3H); RP-HPLC (Hypersil HS, 5 μm, 100 A, 4.6×250 mm; 25%-100% acetonitrile—0.05 M ammonium acetate over 10 min, 1 ml/min) tr 13.12 min.

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. custompurified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-f7c71ebe2db44a70b5b01be8c159771c
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713474B2

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