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Ethyl Acetate → 2-bromo-1-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]ethan-1-one

HRID 1530483
ノート
印刷プレビュー

反応式

HRID 1530483 の反応式
[CH:1]([N:4]1[C:8]([C:9](=[O:11])[CH3:10])=[N:7][CH:6]=[N:5]1)([CH3:3])[CH3:2].[Br-:12].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C(OCC)(=O)C>C(O)(=O)C.C1COCC1.C1CCCCC1>[Br:12][CH2:10][C:9]([C:8]1[N:4]([CH:1]([CH3:3])[CH3:2])[N:5]=[CH:6][N:7]=1)=[O:11]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 8857Ethyl AcetateHCID 149783391-(1-Isopropyl-1H-1,2,4-triazol-5-YL)ethanoneHCID 17977687Phenyltrimethylammonium bromide dibromide

生成物 1

HCID 582044892-bromo-1-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]ethan-1-one収率 36%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒
HCID 8028
Tetrahydrofuran
溶媒
2 回
HCID 8078Cyclohexane溶媒

反応条件

温度
75 °C

実験手順

To a solution of 1-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-ethanone (10 g, 65.3 mmol) in acetic acid (1 mL) and THF (100 mL) was added a solution of PTT (phenyltrimethylammonium tribromide, 24.5 g, 65.3 mmol) in THF (100 mL) over 20 min. The reaction mixture was heated at 75° C. before cooling to RT. The resultant mixture was concentrated in vacuo and the products partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The organic layer was separated, dried (Na2SO4), filtered and concentrated in vacuo to give a residue which was subjected to flash chromatography (SiO2, gradient 0 to 20% ethyl acetate in cyclohexane) to give 2-Bromo-1-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-ethanone as an oil (5.4 g, 36%). 1H NMR δ (ppm) (CDCl3): 7.98 (1H, s), 5.53-5.42 (1H, m), 4.69 (2H, s), 1.52 (6H, d, J=6.63 Hz).

後処理

  1. temperaturebefore cooling to RT
  2. concentrationThe resultant mixture was concentrated in vacuo
  3. customthe products partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution
  4. customThe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a residue which

出典と根拠

ORDレコード
ord-4e153db56de748b192661feaf2e0c477
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09090628B2

反応ノート

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