Iodine → 5-(Benzyloxy)-2-iodophenol

HRID 2277149Notes

Reaction equation

HRID 2277149 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I:16]I>C1(C)C=CC=CC=1.FC(F)(F)C([O-])=O.[Ag+]>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([I:16])=[C:11]([OH:15])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 807IodineHCID 138048Benzyl 3-hydroxyphenyl ether

Product 1

HCID 862518105-(Benzyloxy)-2-iodophenolYield 89.1%

Reagents, catalysts & solvents 2

HCID 76299Silver trifluoroacetateCatalystHCID 1140TolueneSolvent2×

Procedure

To a suspension of 3-(benzyloxy)phenol (5.00 g) and silver trifluoroacetate (5.52 g) in toluene (25 mL) was added dropwise a solution of iodine (6.35 g) in toluene (75 mL) over 30 min under ice-cooling. The reaction mixture was filtered, and to the organic layer were added saturated aqueous sodium hydrogen carbonate solution and saturated brine, and the mixture was extracted with ethyl acetate. The obtained organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (7.26 g).

Workup

  1. temperaturecooling
  2. filtrationThe reaction mixture was filtered
  3. additionto the organic layer were added saturated aqueous sodium hydrogen carbonate solution and saturated brine
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe obtained organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-e62d07b6a27b4541b2ea6492121cb89a
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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