Potassium Carbonate → tert-butyl N-(4-chloro-5-methyl-2-nitrophenyl)carbamate

HRID 498170Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 498170
[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]1[CH:13]=[C:12](Cl)[C:11]([Cl:15])=[CH:10][C:9]=1[N+:16]([O-:18])=[O:17])([CH3:4])([CH3:3])[CH3:2].[C:20](=O)([O-])[O-].[K+].[K+].CB1OB(C)OB(C)O1>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]1[CH:13]=[C:12]([CH3:20])[C:11]([Cl:15])=[CH:10][C:9]=1[N+:16]([O-:18])=[O:17])([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 69489445tert-butyl N-(4,5-dichloro-2-nitrophenyl)carbamate

Produkt 1

HCID 69489578tert-butyl N-(4-chloro-5-methyl-2-nitrophenyl)carbamateAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 218864351,4-Dioxane--water (1/1)Lösungsmittel

Versuchsvorschrift

To a suspension of (4,5-dichloro-2-nitro-phenyl)-carbamic acid tert.-butyl ester (Example A20) (10.0 g, 32.6 mmol), tetrakis(triphenylphosphine)palladium (3.76 g, 3.26 mmol) and potassium carbonate (13.5 g, 97.7 mmol) in dioxane/water (9:1; 100 ml) was added at RT trimethylboroxine (4.53 ml, 32.6 mmol). The reaction mixture was stirred under reflux conditions for 15 h, filtered, evaporated and purified by column chromatography on silica gel (hexane/ethyl acetate 19:1) to yield a light yellow solid (4.45 g, 48%).

Aufarbeitung

  1. filtrationfiltered
  2. customevaporated
  3. custompurified by column chromatography on silica gel (hexane/ethyl acetate 19:1)

Quellen und Nachweise

ORD-Eintrag
ord-f49d5c4f06e14d1ba1719cbece00105c
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06949542B2

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