Ethyl Acetate → (Nonane-1,9-diyl)bis(triphenylphosphanium) dibromide

HRID 2262385Notes

Reaction equation

HRID 2262385 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]Br.[C:12]1([P:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(O[CH2:35][CH3:36])(=O)C>CN1CCCC1=O>[Br-:1].[Br-:1].[C:25]1([P+:18]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][P+:18]([C:36]2[CH:35]=[CH:30][CH:25]=[CH:26][CH:27]=2)([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 11776TriphenylphosphineHCID 206771,9-Dibromononane

Product 1

HCID 71430559(Nonane-1,9-diyl)bis(triphenylphosphanium) dibromideYield 90%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
80 °C

Procedure

28.61 Grams of 1,9-dibromononane and 52.46 g of triphenylphosphine were weighed out and placed in a 500-mL three-necked flask. These compounds were dissolved in 100 mL of N-methylpyrrolidone. This solution was stirred at 80° C. for 5 hours and the resultant reaction mixture was cooled to room temperature. Thereafter, the reaction mixture was poured into 500 mL of ethyl acetate kept being sufficiently stirred. The solid precipitated was collected by suction filtration and washed with 50 mL of ethyl acetate twice. The solid obtained was placed on a Petri dish and dried at room temperature under vacuum until the mass of the solid became constant. As a result, nonamethylenebis(triphenylphosphonium)dibromide was obtained as a white solid in an amount of 73 g (yield: 90%).

Workup

  1. customplaced in a 500-mL three-necked flask
  2. customthe resultant reaction mixture
  3. temperaturewas cooled to room temperature
  4. stirringkept being sufficiently stirred
  5. customThe solid precipitated
  6. filtrationwas collected by suction filtration
  7. washwashed with 50 mL of ethyl acetate twice
  8. customThe solid obtained
  9. customdried at room temperature under vacuum until the mass of the solid

Sources & evidence

ORD record
ord-c637fe886ab04c39ae52ee6f4fd26edf
Source dataset
uspto-grants-2010_12
Patent number
US07851126B2

Reaction notes

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