Magnesium → HCID 22141592, compound

HRID 1826328Notes

Reaction equation

HRID 1826328 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][C:6]=1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[Mg].Br[C:17]1[S:21][C:20]([C:22]2[CH:27]=[C:26]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[C:25]([C:37]3[S:38][C:39](Br)=[CH:40][CH:41]=3)=[CH:24][C:23]=2[O:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])=[CH:19][CH:18]=1>C1COCC1.C(OCC)(=O)C>[CH2:7]([C:6]1[CH:5]=[CH:4][S:3][C:2]=1[C:17]1[S:21][C:20]([C:22]2[CH:27]=[C:26]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[C:25]([C:37]3[S:38][C:39]([C:2]4[S:3][CH:4]=[CH:5][C:6]=4[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[CH:40][CH:41]=3)=[CH:24][C:23]=2[O:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])=[CH:19][CH:18]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 3

HCID 5462224MagnesiumHCID 107548542-Bromo-3-n-octylthiopheneHCID 221415882,2'-[2,5-Bis(octyloxy)-1,4-phenylene]bis(5-bromothiophene)

Product 1

HCID 22141592HCID 22141592, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-bromo-3-octylthiophene (1.800 grams, 6.533 mmol) in 7 milliliters of anhydrous THF was added slowly over a period of 20 minutes to a mechanically stirred suspension of magnesium turnings (0.238 grams, 9.79 mmol) in 3 milliliters of THF in a 250 milliliter round-bottomed flask under an inert argon atmosphere. The resultant mixture was stirred at 60° C. for 4 hours, and then cooled down to room temperature. The resultant mixture was then added via a cannula to a mixture of 1,4-bis(5-bromo-2-thienyl)-2,5-dioctyloxybenzene (1.650 grams, 2.513 mmol) and [1,3-bis(diphenylphosphinopropane]dichloronickel (II) (0.057 gram, 0.105 mmol) in 20 milliliters of anhydrous THF in a 250 milliliter round-bottomed flask under an inert atmosphere, and refluxed for 48 hours. Subsequently, the reaction mixture was diluted with 200 milliliters of ethyl acetate, was washed twice with water and dried with anhydrous magnesium sulfate. A brown solid, obtained after evaporation of the solvent, was purified by column chromotography on silica gel and recrystallized yielding 1,4-bis[5-(3-octyl-2-thienyl)-2-thienyl]-2,5-dioctyloxybenzene as a yellow crystalline product in 30 percent yield.

Workup

  1. washwas washed twice with water
  2. dry with materialdried with anhydrous magnesium sulfate
  3. customA brown solid, obtained
  4. customafter evaporation of the solvent
  5. customwas purified by column chromotography on silica gel
  6. customrecrystallized

Sources & evidence

ORD record
ord-937fbac4c68f4ae5abeaac83ed9012fc
Source dataset
uspto-grants-2006_05
Patent number
US07049629B2

Reaction notes

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