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

HRID 580840Notes

Reaction equation

HRID 580840 reaction equation
[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

Participants

6

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 76299Silver trifluoroacetateCatalystHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-7650f4354124489eb28f311e22550eec
Source dataset
uspto-grants-1999_07
Patent number
US05919781

Reaction notes

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