Iodine → 3-iodo-4-methoxybenzaldehyde

HRID 1360989Notes

Reaction equation

HRID 1360989 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=1.[I:11]I>ClCCl.FC(F)(F)C([O-])=O.[Ag+]>[I:11][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:3]=1[O:2][CH3:1])[CH:7]=[O:8]

Participants

5

Reactant 2

HCID 807IodineHCID 312444-Methoxybenzaldehyde

Product 1

HCID 14943763-iodo-4-methoxybenzaldehydeYield 97.7%

Reagents, catalysts & solvents 2

HCID 76299Silver trifluoroacetateCatalystHCID 6344DichloromethaneSolvent

Procedure

4-Methoxybenzaldehyde (0.5 g, 3.67 mmol) and silver trifluoroacetate (0.92 g, 4.19 mmol) were mixed in dichloromethane (25 mL). Iodine (1.19 g, 4.7 mmol) was added in small portions and the mixture was stirred overnight at room temperature under nitrogen. The mixture was subsequently filtered and the residue washed with DCM. The combined filtrates were treated with an aqueous sodium thiosulfate solution (1 M) until the colour disappeared. Subsequent extraction with dichloromethane (3×20 mL) followed by drying with MgSO4 and evaporation in vacuo afforded 0.94 g of 3-iodo-4-methoxybenzaldehyde.

Workup

  1. filtrationThe mixture was subsequently filtered
  2. washthe residue washed with DCM
  3. additionThe combined filtrates were treated with an aqueous sodium thiosulfate solution (1 M) until the colour
  4. extractionSubsequent extraction with dichloromethane (3×20 mL)
  5. dry with materialby drying with MgSO4 and evaporation in vacuo

Sources & evidence

ORD record
ord-16111e0dcf994cf784ac2dd84382a8a5
Source dataset
uspto-grants-2011_02
Patent number
US07879893B2

Reaction notes

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