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

HRID 583028ノート

反応式

HRID 583028 の反応式
[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

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 76299Silver trifluoroacetate触媒HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒

実験手順

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) δ7.67 (1 H, d, J=2.8 Hz), 7.40 (5 H, m), 7.16 (1 H, dd, J=8.9, 2.8 Hz), 6.82 (1 H, d, J=8.9 Hz), and 5.14 (2 H, s).

後処理

  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

出典と根拠

ORDレコード
ord-fbafbf827bac4828a8de8949ec1e8baf
出典データセット
uspto-grants-1999_07
特許番号
US05929054

反応ノート

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