Iodine → 1-(Benzyloxy)-2-iodo-4-(trifluoromethoxy)benzene

HRID 580840노트

반응식

HRID 580840 반응식
[I:1]I.[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]([F:21])([F:20])[F:19])=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(Cl)(Cl)Cl.ClCCl.FC(F)(F)C([O-])=O.[Ag+]>[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]([F:19])([F:20])[F:21])=[CH:13][C:12]=1[I:1])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

참가 물질

6

반응물 2

HCID 807IodineHCID 215840942-Benzyloxy-5-(trifluoromethoxy)benzene

생성물 1

HCID 113952781-(Benzyloxy)-2-iodo-4-(trifluoromethoxy)benzene수율 101.5%

시약·촉매·용매 3

HCID 76299Silver trifluoroacetate촉매HCID 6212Chloroform용매HCID 6344Dichloromethane용매

실험 절차

Iodine (71.96 g, 0.28 mol) in chloroform was added dropwise to a mixture of 2-benzyloxy-5-(trifluoromethoxy)benzene (Preparation 12, 73.06 g, 0.27 mol) and silver trifluoroacetate (71.57 g, 0.32 mol) in dichloromethane and the mixture was stirred at room temperature for 18 hours. The mixture was filtered through celite, washed with aqueous sodium thiosulfate (5%, 2×2 l), dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with hexane/ethyl acetate, to give the title compound as a colorless oil (108.03 g), containing 11% unreacted 2-benzyloxy-5-(trifluoromethoxy)iodobenzene. 1H NMR (360 MHz, CDCl3) δ 7.67 (1H, d, J=2.8 Hz), 7.40 (5H, m), 7.16 (1H, dd, J=8.9, 2.8 Hz), 6.82 (1H, d, J=8.9 Hz), and 5.14 (2H, s).

후처리

  1. filtrationThe mixture was filtered through celite
  2. washwashed with aqueous sodium thiosulfate (5%, 2×2 l)
  3. dry with materialdried (MgSO4)
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by flash column chromatography on silica gel
  6. washeluting with hexane/ethyl acetate

출처 및 근거

ORD 기록
ord-7650f4354124489eb28f311e22550eec
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05919781

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