Sodium Iodide → 3-bromo-4-(iodomethyl)-1-tert-pentyl-1H-pyrazole

HRID 711044ノート

反応式

HRID 711044 の反応式
[Br:1][C:2]1[C:6]([CH2:7]Cl)=[CH:5][N:4]([C:9]([CH2:12][CH3:13])([CH3:11])[CH3:10])[N:3]=1.[I-:14].[Na+]>CC(C)=O>[Br:1][C:2]1[C:6]([CH2:7][I:14])=[CH:5][N:4]([C:9]([CH2:12][CH3:13])([CH3:11])[CH3:10])[N:3]=1

参加物

4

反応物 2

HCID 5238Sodium IodideHCID 674915603-bromo-4-(chloromethyl)-1-tert-pentyl-1H-pyrazole

生成物 1

HCID 674914913-bromo-4-(iodomethyl)-1-tert-pentyl-1H-pyrazole収率 85%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

To a solution of 3-bromo-4-(chloromethyl)-1-tert-pentyl-1H-pyrazole (725 mg, 2.73 mmol) in acetone (25 mL) was added sodium iodide (4.09 g, 27.3 mmol). The reaction was heated at reflux for 2 hours, then cooled to room temperature and stirred overnight. The solvent was removed in vacuo and the residue was partitioned between ethyl acetate and water. The organic layer was washed with saturated aqueous sodium thiosulfate and brine. The organics were dried over sodium sulfate, filtered, and concentrated to yield the title compound (824 mg, 85%) as a brown oil. 1H NMR (400 MHz, CDCl3, δ): 7.47 (s, 1H), 4.26 (s, 2H), 1.83 (q, J=7.41 Hz, 2H), 1.50 (s, 6H), 0.67 (t, J=7.51 Hz, 3H).

後処理

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 2 hours
  3. customThe solvent was removed in vacuo
  4. customthe residue was partitioned between ethyl acetate and water
  5. washThe organic layer was washed with saturated aqueous sodium thiosulfate and brine
  6. dry with materialThe organics were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-0ad89ed1e50a473892794ab08f92f321
出典データセット
uspto-grants-2015_11
特許番号
US09181252B2

反応ノート

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