(Diethylamino)sulfur trifluoride → 4-(2-Fluoropropan-2-yl)benzenecarbonitrile

HRID 2400554Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2400554
O[C:2]([C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1)([CH3:4])[CH3:3].C(N(S(F)(F)[F:19])CC)C>ClCCl.O>[F:19][C:2]([C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1)([CH3:4])[CH3:3]

Komponenten

5

Edukt 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 5895574-(2-Hydroxypropan-2-yl)benzonitrile

Produkt 1

HCID 595046394-(2-Fluoropropan-2-yl)benzenecarbonitrileAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-(2-hydroxypropan-2-yl)benzonitrile (1.00 g, 6.20 mmol; obtained from 4-(propan-2-yl)benzonitrile according to literature procedure: Synth. Comm. 2006, 36, 2145-2155) in dichloromethane (20 mL) was added diethylamino sulfur trifluoride (DAST; 1.20 g, 7.44 mmol) at a temperature of 0° C. The reaction mixture was allowed to stirr at rt for 2 h, whereupon it was diluted with water and extracted with dichloromethane. The organic extract was washed with water, dried with anhydrous magnesium sulfate and filtered. After evaporation of the solvent, the crude product was purified by MPLC (silica, cyclohexane/ethyl acetate 95:5) to afford the title compound (675 mg, 67%): 1H NMR (400 MHz, CDCl3) δ 7.57 (d, 2H), 7.48 (d, 2H), 1.72 (s, 3H), 1.68 (s, 3H); ES-MS m/z 163, HPLC RT (Method F) 2.12 min.

Aufarbeitung

  1. extractionextracted with dichloromethane
  2. extractionThe organic extract
  3. washwas washed with water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customAfter evaporation of the solvent
  7. customthe crude product was purified by MPLC (silica, cyclohexane/ethyl acetate 95:5)

Quellen und Nachweise

ORD-Eintrag
ord-2791ca9f174645f0840e5deee6f0a3b4
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08796253B2

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