2-Bromothiophene → HCID 22141594, compound

HRID 270242Notes

Reaction equation

HRID 270242 reaction equation
Br[C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[C:5](Br)=[CH:4][C:3]=1[O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].[Mg].Br[C:29]1[S:30][CH:31]=[CH:32][CH:33]=1>O1CCCC1.C(OCC)(=O)C>[S:30]1[CH:31]=[CH:32][CH:33]=[C:29]1[C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[C:5]([C:29]2[S:30][CH:31]=[CH:32][CH:33]=2)=[CH:4][C:3]=1[O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

6

Reactant 3

HCID 138512-BromothiopheneHCID 27534941,4-Dibromo-2,5-bis(octyloxy)benzeneHCID 5462224Magnesium

Product 1

HCID 22141594HCID 22141594, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1,4-dibromo-2,5-dioctyloxybezene (6.580 grams, 13.365 mmol) in 15 milliliters of anhydrous tetrahydrofuran (THF) was added slowly over a period of 20 minutes to a mechanically stirred suspension of magnesium turnings (0.975 gram, 40.095 mmol) in 5 milliliters of THF in a 250 milliliter round-bottomed flask under an inert argon atmosphere. The resultant mixture was stirred at 60° C. for 3.5 hours. Subsequently, the resulting mixture was added to a mixture of 2-bromothiophene (5.447 grams, 33.412 mmol) and [1,3-bis(diphenylphosphinoethane]dichloronickel (II) (0.350 gram, 0.663 mmol) in 45 milliliters of anhydrous THF in a 250 milliliter round-bottomed flask under an inert atmosphere, and refluxed for 24 hours. Thereafter, the reaction mixture was diluted with 200 milliliters of ethyl acetate, washed twice with water and then dried with anhydrous magnesium sulfate. A brown solid, obtained after evaporation of the solvent, was purified by column chromatography on silica gel and recrystallization yielding 1,4-bis(2-thienyl)-2,5-dioctyloxybenzene as a light yellow crystalline product in 45 percent yield.

Workup

  1. washwashed 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 chromatography on silica gel and recrystallization

Sources & evidence

ORD record
ord-eb64baf4de0c4240b1594078c0b45931
Source dataset
uspto-grants-2008_11
Patent number
US07449542B2

Reaction notes

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