4-Iodobenzaldehyde → 4-Cyclobutylbenzaldehyde

HRID 1485050Notes

Reaction equation

HRID 1485050 reaction equation
I[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[Br-].[CH:11]1([Zn+])[CH2:14][CH2:13][CH2:12]1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.O1CCCC1>[CH:11]1([C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)[CH2:14][CH2:13][CH2:12]1

Participants

6

Reactant 2

HCID 966574-IodobenzaldehydeHCID 178419766HCID 178419766, compound

Product 1

HCID 571743534-Cyclobutylbenzaldehyde

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 4-iodobenzaldehyde (500 mg), bis(triphenylphosphine)palladium(II) dichloride (75.6 mg), copper(I) iodide (24.6 mg) and dehydrated tetrahydrofuran (10.0 mL), cyclobutylzinc bromide (0.5 mol/L, solution in tetrahydrofuran, 6.46 mL) was added and the mixture was stirred in a sealed tube at 60° C. for 14 hours. After cooling to room temperature, the precipitate was removed by filtration through Celite (registered trademark). The filtrate was concentrated under reduced pressure and thereafter purified by silica gel column chromatography (n-hexane:ethyl acetate=98:2-90:10) to give the titled compound as a colorless oil (225 mg).

Workup

  1. additionwas added
  2. temperatureAfter cooling to room temperature
  3. customthe precipitate was removed by filtration through Celite (registered trademark)
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. custompurified by silica gel column chromatography (n-hexane:ethyl acetate=98:2-90:10)

Sources & evidence

ORD record
ord-4768ea2e423a4be787bc226767c737f6
Source dataset
uspto-grants-2016_08
Patent number
US09422240B2

Reaction notes

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