Water → Ethyl2-cyano-5-fluorobenzoate

HRID 455290Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 455290
Br[C:2]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.[CH3:34][N:35](C=O)C>[C-]#N.[Zn+2].[C-]#N.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:34]([C:2]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:35]

Komponenten

7

Edukt 4

HCID 962WaterHCID 6228DimethylformamideHCID 11776TriphenylphosphineHCID 15037299Ethyl 2-bromo-5-fluorobenzoate

Produkt 1

HCID 55265172Ethyl2-cyano-5-fluorobenzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11186Zinc cyanide (Zn(CN)2)KatalysatorHCID 9811564Bis(dibenzylideneacetone)palladiumKatalysator

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

Zinc cyanide (26.5 g; 0.225 mol) and Pd2(dba)3 (1.9 g; 3.4 mmol) were added to a solution of ethyl 2-bromo-5-fluorobenzoate (27.9 g; 0.112 mol) in DMF (71 ml). Triphenyl phosphine (2.9 g; 11 mmol) was added and then the reaction mixture was stirred at 130° C. under nitrogen atmosphere for 4 hours. The mixture was poured out into H2O (300 ml) and then extracted with EtOAc (200 ml). The organic layer was separated, washed with H2O (2×100 ml), brine (100 ml), dried (MgSO4), filtered and the solvent was evaporated.

Aufarbeitung

  1. extractionextracted with EtOAc (200 ml)
  2. customThe organic layer was separated
  3. washwashed with H2O (2×100 ml), brine (100 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-8885373191a242848b5bc37f044c440d
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08497270B2

Notizen zur Reaktion

Wird geladen…