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

HRID 269551Notes

Reaction equation

HRID 269551 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[B-](F)(F)F.F[B-](F)(F)F.ClC[N+]12CC[N+](F)(CC1)CC2.[I:40]I>C(#N)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:16])([F:17])[F:18])=[CH:11][C:10]=1[I:40])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 807IodineHCID 2724933SelectfluorHCID 27981684-Benzyloxybenzotrifluoride

Product 1

HCID 211129271-(Benzyloxy)-2-iodo-4-(trifluoromethyl)benzeneYield 158.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4(benzyloxy)benzotrifluoride (12.71 g, 50.4 mmol) in acetonitrile (300 ml) was stirred under nitrogen and 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (17.75 g, 50.4 mmol) and iodine (6.4 g, 25.2 mmol) added. The mixture was stirred at room temperature for 88 h. The solvent was evaporated and the residue partitioned between ethyl acetate (400 ml) and water (400 ml). The organic layer was washed with water, dried (MgSO4) and evaporated to an orange oil which was purified by flash chromatography (silica gel, 5% ethyl acetate:isohexane) to give the title compound as an orange oil (15.07 g, 79%)

Workup

  1. customThe solvent was evaporated
  2. customthe residue partitioned between ethyl acetate (400 ml) and water (400 ml)
  3. washThe organic layer was washed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated to an orange oil which
  6. customwas purified by flash chromatography (silica gel, 5% ethyl acetate:isohexane)

Sources & evidence

ORD record
ord-036952fdfd3e46c183faa23186a493cf
Source dataset
uspto-grants-2008_11
Patent number
US07446222B2

Reaction notes

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