Potassium Iodide → 1-(Cyclopropyloxy)-2-iodo-4-(trifluoromethoxy)benzene

HRID 580844노트

반응식

HRID 580844 반응식
N([O-])=O.[Na+].[CH:5]1([O:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][C:10]=2N)[CH2:7][CH2:6]1.[I-:21].[K+]>O.Cl>[CH:5]1([O:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][C:10]=2[I:21])[CH2:7][CH2:6]1

참가 물질

6

반응물 3

HCID 4875Potassium IodideHCID 215840842-Cyclopropoxy-5-(trifluoromethoxy)benzeneamineHCID 23668193Sodium Nitrite

생성물 1

HCID 117596921-(Cyclopropyloxy)-2-iodo-4-(trifluoromethoxy)benzene수율 88%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 962Water용매2회

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온도
0 °C

실험 절차

An ice-cooled solution of sodium nitrite (3.55 g, 51 mmol) in water (10 mL) was added dropwise to a stirred, cooled (0° C.) solution of 2-cyclopropoxy-5-(trifluoromethoxy)benzeneamine (Description 7, 4.8 g, 20.6 mmol) in aqueous hydrochloric acid (5M, 300 mL), maintaining the internal temperature at 0° C. The mixture was stirred at 0° C. for 30 min., then potassium iodide (8.55 g, 51.5 mmol) in water (10 mL) was added dropwise, maintaining the internal temperature at 0° C. The mixture was stirred at 0° C. for 30 min., then allowed to warm up to room temperature and stirred until nitrogen evolution ceased. The mixture was extracted with ether, the organic fraction was washed with aqueous sodium thiosulfate (10%), dried (MgSO4), and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with hexane/Et2O (98:2 increasing to 95:5), to give the title compound as a colourless oil (6.23 g, 88%). 1H NMR (360 MHz, CDCl3) δ 7.62 (1H, d, J 2.4 Hz), 7.20 (1H, dd, J 9.1, 2.4 Hz), 7.15 (1H, d, J 9.1 Hz), 3.80 (1H, m), and 0.83 (4H, m).

후처리

  1. additionwas added dropwise to a stirred
  2. temperaturemaintaining the internal temperature at 0° C
  3. stirringThe mixture was stirred at 0° C. for 30 min.
  4. temperatureto warm up to room temperature
  5. stirringstirred until nitrogen evolution
  6. extractionThe mixture was extracted with ether
  7. washthe organic fraction was washed with aqueous sodium thiosulfate (10%)
  8. dry with materialdried (MgSO4)
  9. customthe solvent was evaporated under reduced pressure
  10. customThe residue was purified by flash column chromatography on silica gel
  11. washeluting with hexane/Et2O (98:2 increasing to 95:5)

출처 및 근거

ORD 기록
ord-46a35f80249e4545826e3a68495fe768
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05919781

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