Potassium Phosphate, Tribasic → Ethyl 4-nitro-[1,1'-biphenyl]-3-carboxylate

HRID 1054230Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1054230
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:16]1(B(O)O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N+:13]([C:5]1[CH:4]=[CH:3][C:2]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:12][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8])([O-:15])=[O:14]

Komponenten

8

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 603450Ethyl 5-chloro-2-nitrobenzoate

Produkt 1

HCID 90258855Ethyl 4-nitro-[1,1'-biphenyl]-3-carboxylateAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

To a stirring solution of ethyl 5-chloro-2-nitrobenzoate (2 g, 8.71 mmol) and phenylboronic acid (2.124 g, 17.42 mmol) in DMF (20 ml) was added K3PO4 (2.77 g, 13.07 mmol), palladium acetate (0.098 g, 0.436 mmol) and tetrabutylammonium bromide (4.21 g, 13.07 mmol). Reaction mixture was heated at 95° 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 89% 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-8bae050575614452a28ba348ee0dd43b
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394300B2

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