Triethylamine → 4-[(4-Hexylphenyl)ethynyl]benzaldehyde

HRID 735932Notes

Reaction equation

HRID 735932 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[C:10]([C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:14][CH:13]=1)#[CH:11].CCN(CC)CC>C1COCC1.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]Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:18]([C:15]1[CH:14]=[CH:13][C:12]([C:10]#[C:11][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)=[CH:17][CH:16]=1)[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 707414-BromobenzaldehydeHCID 27751291-Ethynyl-4-hexylbenzene

Product 1

HCID 112892864-[(4-Hexylphenyl)ethynyl]benzaldehydeYield 98.6%

Reagents, catalysts & solvents 4

HCID 11776TriphenylphosphineCatalystHCID 24593copper(I) bromideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-bromobenzaldehyde (5.00 g, 27.0 mmol), 1-ethynyl-4-hexylbenzene (6.29 g, 33.4 mmol), Et3N (4.70 mL, 33.4 mmol), bis(triphenylphosphine)palladium chloride (950 mg, 1.35 mmol) and triphenylphosphine (180 mg, 0.68 mmol) in anhydrous THF (100 mL) was stirred at rt for 30 min under inert atmosphere. Then copper(I) bromide (82 mg, 0.43 mmol) was added and the resulting mixture was stirred overnight at rt. The solvent was evaporated off. The residue was dissolved in Et2O (100 mL), washed with water (50 mL), dried over MgSO4 and the solvent was removed under reduced pressure. The resulting brown solid was triturated in hexane (25 mL), filtered off and washed with hexane to give the title compound as a beige solid (7.73 g, 91%). HPLC (Condition A), Rt: 5.88 min (HPLC purity: 91.9%).

Workup

  1. stirringthe resulting mixture was stirred overnight at rt
  2. customThe solvent was evaporated off
  3. dissolutionThe residue was dissolved in Et2O (100 mL)
  4. washwashed with water (50 mL)
  5. dry with materialdried over MgSO4
  6. customthe solvent was removed under reduced pressure
  7. customThe resulting brown solid was triturated in hexane (25 mL)
  8. filtrationfiltered off
  9. washwashed with hexane

Sources & evidence

ORD record
ord-c5bbc70b54144cd691e27e94c5b42525
Source dataset
uspto-grants-2009_09
Patent number
US07592477B2

Reaction notes

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