1-Bromo-4-isopropylbenzene → 5,5'-Bis(4-isopropylphenyl)-2,2'-bithiophene

HRID 2222067Notes

Reaction equation

HRID 2222067 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[S:10][C:9]([C:11]2[S:12][C:13]([Sn](CCCC)(CCCC)CCCC)=[CH:14][CH:15]=2)=[CH:8][CH:7]=1)CCC.Br[C:38]1[CH:43]=[CH:42][C:41]([CH:44]([CH3:46])[CH3:45])=[CH:40][CH:39]=1>CN(C)C=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:44]([C:41]1[CH:42]=[CH:43][C:38]([C:13]2[S:12][C:11]([C:9]3[S:10][C:6]([C:38]4[CH:43]=[CH:42][C:41]([CH:44]([CH3:46])[CH3:45])=[CH:40][CH:39]=4)=[CH:7][CH:8]=3)=[CH:15][CH:14]=2)=[CH:39][CH:40]=1)([CH3:46])[CH3:45]

Participants

5

Reactant 2

HCID 114621-Bromo-4-isopropylbenzeneHCID 10533055Agn-PC-0N63KQ

Product 1

HCID 687616785,5'-Bis(4-isopropylphenyl)-2,2'-bithiopheneYield 61.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 1.8 g of 5,5′-bis(tributylstannyl)-2,2′-bithiophene, 1.3 g of 1-bromo-4-isopropylbenzene, and 80 mg of Pd(PPh3)4 in 35 milliliters (“mL”) of N,N-dimethylformamide was heated at 70° C. for 2 days under nitrogen. After cooling, 0.6 g of yeliow-green solid was obtained after washing with methanol and ether, verified pure by nuclear magnetic resonance spectroscopy (“NMR”), and used directly for film and crystal studies.

Workup

  1. temperatureAfter cooling

Sources & evidence

ORD record
ord-d1b301ef349f4d06b737435f840c765a
Source dataset
uspto-grants-2008_05
Patent number
US07371605B2

Reaction notes

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