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

HRID 2400554ノート

反応式

HRID 2400554 の反応式
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]

参加物

5

反応物 2

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

生成物 1

HCID 595046394-(2-Fluoropropan-2-yl)benzenecarbonitrile収率 67%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-2791ca9f174645f0840e5deee6f0a3b4
出典データセット
uspto-grants-2014_08
特許番号
US08796253B2

反応ノート

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