Triethylamine → 1-Chloro-2-nitro-4-phenoxybenzene

HRID 1241937Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1241937
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 691274-Chloro-3-nitrophenol

Produkt 1

HCID 219378011-Chloro-2-nitro-4-phenoxybenzeneAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8895Cupric acetateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 4-chloro-3-nitro-phenol (5.00 g, 28.81 mmol), phenylboronic acid (7.03 g, 57.62 mmol), copper(II) acetate (5.23 g, 28.81 mmol) and 4 Å molecular sieves (0.5 g) in dichloromethane (200 mL) and triethylamine (20.08 mL, 144.04 mmol) was placed in a round bottomed flask. The resulting suspension was stirred under a dry ambient atmosphere at room temperature for 4 days. The mixture was filtered through diatomaceous earth and the solvent was evaporated. The resulting residue was re-dissolved in EtOAc, adhered to silica gel and flash chromatographed (2% EtOAc/hexane) to give 1-chloro-2-nitro-4-phenoxy-benzene as a yellow oil (1.53 g, 22.0% yield).

Aufarbeitung

  1. filtrationThe mixture was filtered through diatomaceous earth
  2. customthe solvent was evaporated
  3. dissolutionThe resulting residue was re-dissolved in EtOAc
  4. customchromatographed (2% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-3bc64fe1701f402a9da37f67d0e39017
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07115644B2

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