Water → 4-Bromo-1-(4-butylphenylethynyl)-2-ethylbenzene

HRID 707745Notes

Reaction equation

HRID 707745 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[CH2:9][CH3:10].[CH2:11]([C:17]1[CH:22]=[CH:21][C:20]([C:23]#[CH:24])=[CH:19][CH:18]=1)[CH2:12][CH2:13][CH2:14]CC.O.CCCCCCC>C(N(CC)CC)C.[Cu]I.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>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:24]#[C:23][C:20]2[CH:21]=[CH:22][C:17]([CH2:11][CH2:12][CH2:13][CH3:14])=[CH:18][CH:19]=2)=[C:3]([CH2:9][CH3:10])[CH:4]=1

Participants

8

Reactant 4

HCID 962WaterHCID 8900HeptaneHCID 27613964-Bromo-2-ethyl-1-iodobenzeneHCID 27751291-Ethynyl-4-hexylbenzene

Product 1

HCID 676077494-Bromo-1-(4-butylphenylethynyl)-2-ethylbenzene

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

20 g (64.3 mmol) of 1-iodo-2-ethyl-4-bromobenzene and 12 g (64.3 mmol) of 4-n-hexylphenylacetylene are initially introduced in 300 ml of triethylamine, 250 mg (1.3 mmol) of copper(I) iodide and 900 mg (1.3 mmol) of bis(triphenylphosphine)palladium(II) chloride are added, and the mixture is stirred at RT for 3 h and subsequently refluxed for 1 h. The batch is cooled, water and heptane are added, and the phases are separated. The organic phase is washed with saturated sodium chloride soln., dried over sodium sulfate, filtered and evaporated in a rotary evaporator. The residue is purified by column chromatography (SiO2, heptane); the product is obtained as a colourless oil.

Workup

  1. temperaturesubsequently refluxed for 1 h
  2. temperatureThe batch is cooled
  3. customthe phases are separated
  4. washThe organic phase is washed with saturated sodium chloride soln
  5. dry with material, dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated in a rotary evaporator
  8. customThe residue is purified by column chromatography (SiO2, heptane)
  9. customthe product is obtained as a colourless oil

Sources & evidence

ORD record
ord-00472664c99d416fbb38272abdb39583
Source dataset
uspto-grants-2015_11
Patent number
US09175219B2

Reaction notes

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