Dimethylformamide → 4'-Chloro-2-nitro-1,1'-biphenyl

HRID 1914405Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1914405
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[Cl:11][C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CN(C)C=O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])=[CH:14][CH:13]=1

Komponenten

8

Edukt 4

HCID 6228DimethylformamideHCID 113411-Bromo-2-nitrobenzeneHCID 62657Potassium Phosphate, TribasicHCID 742994-Chlorophenylboronic acid

Produkt 1

HCID 2355494'-Chloro-2-nitro-1,1'-biphenylAusbeute 74,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A mixed solution of 10 g of 2-bromonitrobenzene, 8.5 g of 4-chlorophenylboronic acid, 25.4 g of tripotassium phosphate, 3.9 g of tetrabutylammonium bromide, 270 mg of palladium acetate and 150 ml of dimethylformamide was heated and stirred under a nitrogen gas stream at 130° C. for 3 hours. The solution was cooled to room temperature and 100 ml of water was poured into the solution, followed by extraction with 150 ml of ethyl acetate. The organic layer was washed twice with 100 ml of water, dried over magnesium sulfate and then evaporated. The concentrate was purified by silica gel column chromatography and then vacuum-dried to obtain 8.6 g of 2-(4-chlorophenyl)nitrobenzene.

Aufarbeitung

  1. temperatureThe solution was cooled to room temperature
  2. extractionfollowed by extraction with 150 ml of ethyl acetate
  3. washThe organic layer was washed twice with 100 ml of water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe concentrate was purified by silica gel column chromatography
  7. customvacuum-dried

Quellen und Nachweise

ORD-Eintrag
ord-6f9bb8e249a64b20b03061e29405bb78
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08610345B2

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