Phenol → Ethyl 2-nitro-5-phenoxybenzoate

HRID 1054229

Reaktionsgleichung

Reaktionsgleichung von HRID 1054229
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:13]([O-:15])=[O:14])=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8].C([O-])([O-])=O.[K+].[K+].[C:22]1([OH:28])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C=O)C.O>[N+:13]([C:5]1[CH:4]=[CH:3][C:2]([O:28][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:12][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8])([O-:15])=[O:14]

Komponenten

6

Edukt 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 603450Ethyl 5-chloro-2-nitrobenzoate

Produkt 1

HCID 57796884Ethyl 2-nitro-5-phenoxybenzoateAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

To a stirring suspension of ethyl 5-chloro-2-nitrobenzoate (15 g, 65.3 mmol) and K2CO3 (13.54 g, 98 mmol) in DMF (5 ml) was added phenol (6.76 g, 71.9 mmol). Reaction mixture was heated at 130° C. for 16 h. Reaction mixture was diluted with water and extracted with EtOAc. The organic layer was separated and distilled out to get crude product which was column purified using 10% EtOAC in hexane to get the titled compound in 36% yield.

Aufarbeitung

  1. customReaction mixture
  2. customReaction mixture
  3. extractionextracted with EtOAc
  4. customThe organic layer was separated
  5. distillationdistilled out
  6. customto get crude product which
  7. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-b7490241d3014ddeab3ce446bfb37f76
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394300B2

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