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

HRID 2400554Notes

Reaction equation

HRID 2400554 reaction equation
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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-2791ca9f174645f0840e5deee6f0a3b4
Source dataset
uspto-grants-2014_08
Patent number
US08796253B2

Reaction notes

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