Iodine → 4-Benzyloxy-2-iodo-5-methoxybenzaldehyde

HRID 2381229Notes

Reaction equation

HRID 2381229 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][C:10]=1[O:17][CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I:19]I>FC(F)(F)C([O-])=O.[Ag+].C(Cl)Cl>[CH2:1]([O:8][C:9]1[C:10]([O:17][CH3:18])=[CH:11][C:12]([CH:13]=[O:14])=[C:15]([I:19])[CH:16]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 807IodineHCID 755064-(Benzyloxy)-3-methoxybenzaldehyde

Product 1

HCID 127730874-Benzyloxy-2-iodo-5-methoxybenzaldehydeYield 86.9%

Reagents, catalysts & solvents 2

HCID 76299Silver trifluoroacetateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-benzyloxy-3-methoxybenzaldehyde (10 g), silver trifluoroacetate (11.4 g) and methylene chloride (105 mL) was added iodine (13.1 g) at room temperature. After stirring for 2 hours, the mixture was passed through a layer of Celite (registered mark). The filtrate was washed with an aqueous solution of sodium hydrogen sulfite and brine successively, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was triturated with methanol: water=4:1 to give the title compound (13.2 g).

Workup

  1. washThe filtrate was washed with an aqueous solution of sodium hydrogen sulfite and brine successively
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was triturated with methanol

Sources & evidence

ORD record
ord-18d474ec6f3f4766a76590efde581ab7
Source dataset
uspto-grants-2012_09
Patent number
US08258162B2

Reaction notes

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