Dimethylformamide → Methyl 3-cyano-5-(trifluoromethyl)benzoate

HRID 1640146Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1640146
Br[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH3:16][N:17](C=O)C>[C-]#N.[Zn+2].[C-]#N.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:16]([C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])#[N:17]

Komponenten

5

Edukt 2

HCID 6228DimethylformamideHCID 18942156Methyl 3-bromo-5-(trifluoromethyl)benzoate

Produkt 1

HCID 58902345Methyl 3-cyano-5-(trifluoromethyl)benzoateAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11186Zinc cyanide (Zn(CN)2)KatalysatorHCID 178418397HCID 178418397, VerbindungKatalysator

Versuchsvorschrift

A mixture of methyl 3-bromo-5-(trifluoromethyl)benzoate (5.10 g, 0.0180 mol), zinc cyanide (1.26 g, 0.0107 mol) and tetrakis(triphenylphosphine)palladium(0) (0.910 g, 0.000787 mol) in DMF (50 mL) was subjected to MWI for 20 min at 230° C. The solvent was evaporated and the residue was suspended in EtOAc. The organic solution was and washed with 1N HCl, water and brine, dried and concentrated. The residue was purified by column chromatography to give methyl 3-cyano-5-(trifluoromethyl)benzoate (2.67 g, 64%) as white solid. 1H NMR (400 MHz, CDCl3) δ: 8.50-8.52 (m, 2H), 8.09 (m, 1H), and 4.03 (s, 3H).

Aufarbeitung

  1. customThe solvent was evaporated
  2. washwashed with 1N HCl, water and brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-63466416da5b4ec0a31c39667e5b3913
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08110687B2

Notizen zur Reaktion

Wird geladen…