Iodine → 1-(Benzyloxy)-2-iodo-4-(trifluoromethoxy)benzene
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]=1Participants
Procedure
Iodine (71.96 g, 0.28 mol) in chloroform was added dropwise to a mixture of 2-benzyloxy-5-(trifluoromethoxy)benzene (Description 102, 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 h. 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/EtOAc, 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
- filtrationThe mixture was filtered through celite
- washwashed with aqueous sodium thiosulfate (5%, 2×2 l)
- dry with materialdried (MgSO4)
- customthe solvent was evaporated under reduced pressure
- customThe residue was purified by flash column chromatography on silica gel
- washeluting with hexane/EtOAc
Sources & evidence
- ORD record
- ord-f7d1a0f3b4f14b7e8d0dfacacf09da87
- Source dataset
- uspto-grants-2000_06
- Patent number
- US06071927
Reaction notes
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