Benzene → HCID 67420294, compound

HRID 1521792Notes

Reaction equation

HRID 1521792 reaction equation
[Br:1][C:2]1[CH:7]=[C:6](I)[C:5]([Br:9])=[CH:4][C:3]=1I.[CH:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH2:17]=[CH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]CCCC.O.[CH:30](NC(C)C)(C)[CH3:31]>[Cu](I)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:1][C:2]1[CH:7]=[C:6]([C:17]#[C:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:5]([Br:9])=[CH:4][C:3]=1[C:30]#[C:31][CH2:11][CH2:16][CH2:15][CH2:14][CH2:13][CH3:12]

Participants

8

Reactant 5

HCID 241BenzeneHCID 962WaterHCID 7912DiisopropylamineHCID 81831-DodeceneHCID 111237711,4-Dibromo-2,5-diiodobenzene

Product 1

HCID 67420294HCID 67420294, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalyst

Procedure

Under nitrogen atmosphere, 1,4-dibromo-2,5-diiodobenzene (3.0 g, 6.2 mmol) was dissolved in diisopropylamine (45 ml) and anhydrous benzene (45 ml), followed by stirring for 30 minutes. Copper iodide (235 mg, 0.12 mmol), PdCl2(PPh3)2 (430 mg, 0.61 mmol), and 1-dodecene (1.9 ml, 12.9 mmol) were added to the mixture, followed by stirring at room temperature for 14 hours. The reaction liquid was poured into water and extracted with chloroform, and the obtained organic layer was washed with 200 ml of water three times. The resulting organic layer was dried over anhydrous sodium sulfate and purified by a column chromatography (silica gel and methylene chloride:hexane=1:3), followed by recrystallization in ethanol, thereby colorless powdery 1,4-dibromo-2,5-bis(octyne-1-yl)benzene was obtained (1.56 g, yield: 56%).

Workup

  1. stirringby stirring at room temperature for 14 hours
  2. customThe reaction liquid
  3. extractionextracted with chloroform
  4. washthe obtained organic layer was washed with 200 ml of water three times
  5. dry with materialThe resulting organic layer was dried over anhydrous sodium sulfate
  6. custompurified by a column chromatography (silica gel and methylene chloride:hexane=1:3)
  7. customfollowed by recrystallization in ethanol

Sources & evidence

ORD record
ord-63481d10a579495b9235690a4b6ceb8c
Source dataset
uspto-grants-2015_07
Patent number
US09073938B2

Reaction notes

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