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

HRID 886199
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HRID 886199 반응식
[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]
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참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 176Acetic Acid용매
HCID 8028
Tetrahydrofuran
용매
2회
HCID 8078Cyclohexane용매

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온도
75 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c6e38fa9df3a42168696e924f75a296b
출처 데이터셋
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08242104B2

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