Dimethylformamide → 3-(Hydroxymethyl)-5-(trifluoromethyl)benzonitrile

HRID 391407Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 391407
Br[C:2]1[CH:3]=[C:4]([CH2:12][OH:13])[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[CH3:14][N:15](C)C=O>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C-]#N.[Zn+2].[C-]#N>[OH:13][CH2:12][C:4]1[CH:3]=[C:2]([CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=1)[C:14]#[N:15]

Komponenten

5

Edukt 2

HCID 6228DimethylformamideHCID 29919767[3-Bromo-5-(trifluoromethyl)phenyl]methanol

Produkt 1

HCID 117012213-(Hydroxymethyl)-5-(trifluoromethyl)benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11186Zinc cyanide (Zn(CN)2)KatalysatorHCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysator

Versuchsvorschrift

(3-Bromo-5-(trifluoromethyl)phenyl)methanol (1.4 g, 5.5 mmol), tetrakis(triphenylphosphine) palladium(0) (0.64, 0.55 mmol) and zinc cyanide (388 mg, 3.31 mmol) were combined in dimethylformamide (6 mL). The reaction mixture degassed repeatedly using the freeze-thaw method. After warming to room temperature, the reaction was heated at 90° C. for 1 h, cooled to room temperature and concentrated. The crude product was dissolved in ethyl acetate, washed with water (2×), 1 N hydrochloric acid (2×), brine (2×), dried over sodium sulfate, and concentrated. Flash chromatography on silica gel gave 0.37 g (33%). LC/MS (HPLC method 3): tR=2.06 min, 202.02 (MH)+.

Aufarbeitung

  1. customThe reaction mixture degassed repeatedly
  2. temperaturethe reaction was heated at 90° C. for 1 h
  3. temperaturecooled to room temperature
  4. concentrationconcentrated
  5. dissolutionThe crude product was dissolved in ethyl acetate
  6. washwashed with water (2×), 1 N hydrochloric acid (2×), brine (2×)
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customFlash chromatography on silica gel gave 0.37 g (33%)

Quellen und Nachweise

ORD-Eintrag
ord-2434f595a78d4ca38fa68bbdbd39bf82
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383821B2

Notizen zur Reaktion

Wird geladen…