2-Bromobenzaldehyde → 2-((4-Methoxyphenyl)ethynyl)benzaldehyde

HRID 884709Notes

Reaction equation

HRID 884709 reaction equation
Br[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]#[CH:19])=[CH:14][CH:13]=1>C(N(CC)CC)C.[Cu]I>[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]#[C:19][C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[CH:4]=[O:5])=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 811292-BromobenzaldehydeHCID 2510201-Ethynyl-4-methoxybenzene

Product 1

HCID 129972402-((4-Methoxyphenyl)ethynyl)benzaldehydeYield 89%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-bromobenzaldehyde (1.85 g, 10 mmol) and 4-methoxyphenyl acetylene (1.58 g, 12 mmol) in 40 mL of triethylamine were added dichlorobis(triphenylphosphine) palladium(II) (140 mg, 2 mol %) and copper(I) iodide (20 mg, 1 mol %). The reaction mixture was heated at 50° C. under nitrogen for 3 h. The reaction mixture was cooled to room temperature and the ammonium salt was removed by filtration. The filtrate was concentrated under reduced pressure. Purification of the crude compound by column chromatography (SilicaGel 230-400 mesh; 10% ethyl acetate in hexanes as eluent) afforded of 2-(4-methoxy phenylethynyl)benzaldehyde (2.1 g, 89%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe ammonium salt was removed by filtration
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customPurification of the crude compound by column chromatography (SilicaGel 230-400 mesh; 10% ethyl acetate in hexanes as eluent)

Sources & evidence

ORD record
ord-694789bc83ec4220855484417f92c803
Source dataset
uspto-grants-2012_08
Patent number
US08242130B2

Reaction notes

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