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

HRID 2400554노트

반응식

HRID 2400554 반응식
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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-2791ca9f174645f0840e5deee6f0a3b4
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08796253B2

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