2,5-Dichlorophenol → 4-(2,5-Dichlorophenoxy)-3-nitrobenzonitrile

HRID 1946847

Reaktionsgleichung

Reaktionsgleichung von HRID 1946847
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[OH:9].Cl[C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][C:12]=1[N+:19]([O-:21])=[O:20].C([O-])([O-])=O.[K+].[K+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[O:9][C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][C:12]=1[N+:19]([O-:21])=[O:20]

Komponenten

5

Edukt 3

HCID 662,5-DichlorophenolHCID 11430Potassium CarbonateHCID 13655Benzonitrile, 4-chloro-3-nitro-

Produkt 1

HCID 595489424-(2,5-Dichlorophenoxy)-3-nitrobenzonitrileAusbeute 81,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2,5-Dichlorophenol (17.86 g, 109.54 mmol) and 4-chloro-3-nitrobenzonitrile (10.00 g, 54.77 mmol) were combined with K2CO3 (37.85 g, 273.85 mmol) in THF (300 mL). The reaction mixture was refluxed for 48 hrs and then the solid was filtered over a bed of Celite. After rinsing the residue with copious amounts of DCM, the filtrate was concentrated to produce a yellow solid. The solid was triturated with minimal DCM and collected via vacuum filtration to yield compound 34 (13.84 g, 81.7% yield, 100.0% pure). 1H NMR (500 MHz, DMSO-d6): δ 8.73 (s, 1H), 8.12 (dd, J1=9 Hz, J2=2 Hz, 1H), 7.73 (d, J=9 Hz, 1H), 7.65 (d, J=2 Hz, 1H), 7.48 (dd, J1=9 Hz, J2=2 Hz, 1H), 7.21 (d, J=9 Hz, 1H).

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 48 hrs
  2. filtrationthe solid was filtered over a bed of Celite
  3. washAfter rinsing the residue with copious amounts of DCM
  4. concentrationthe filtrate was concentrated
  5. customto produce a yellow solid
  6. customThe solid was triturated with minimal DCM
  7. filtrationcollected via vacuum filtration

Quellen und Nachweise

ORD-Eintrag
ord-c6845f4a525f42d7a7b4b65c46ef0020
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399456B2

Verknüpfte Notizen

Wird geladen…