Hydrochloric Acid → 4-Iodobenzaldehyde

HRID 876108Notes

Reaction equation

HRID 876108 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[I-:10].[K+].CN(C)C=O.Cl>[Cu](I)I.C(OCC)(=O)C>[I:10][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 6228DimethylformamideHCID 707414-Bromobenzaldehyde

Product 1

HCID 966574-Iodobenzaldehyde

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

8.0 g (43.2 mmol) of 4-bromobenzaldehyde, 107.6 g (0.65 mmol) of potassium iodide, 41.1 g (0.22 mmol) of copper iodide and 130 mL of dimethylformamide (DMF) were put in a 300 mL three-neck flask, and refluxed in a nitrogen atmosphere for 3 hours. After it was put back at a room temperature, 1N of hydrochloric acid and ethyl acetate were added, and stirred for 1 hour. It was filtered to remove potassium iodide and copper iodide, and the filtrate was washed with sodium sulfate and water, and dried with magnesium sulfate. It was distilled under a reduced pressure to obtain 4-iodobenzaldehyde (compound A). A synthesis scheme is shown below.

Workup

  1. temperaturerefluxed in a nitrogen atmosphere for 3 hours
  2. customwas put back at a room temperature
  3. filtrationIt was filtered
  4. customto remove potassium iodide and copper iodide
  5. washthe filtrate was washed with sodium sulfate and water
  6. dry with materialdried with magnesium sulfate
  7. distillationIt was distilled under a reduced pressure

Sources & evidence

ORD record
ord-19ebcd1cd979458f8c4841dce600de74
Source dataset
uspto-grants-2015_03
Patent number
US08986854B2

Reaction notes

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