2,5-Dibromothiophene → Stannane, tributyl(5'-hexyl[2,2'-bithiophen]-5-yl)-

HRID 2098984Notes

Reaction equation

HRID 2098984 reaction equation
[CH2:1]([Sn:5]([CH2:27][CH2:28][CH2:29][CH3:30])([CH2:23][CH2:24][CH2:25][CH3:26])[C:6]1[S:7][C:8]([C:11]2C=C[C:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:13][CH:12]=2)=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4].BrC1[S:33]C(Br)=CC=1>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.C1(C)C=CC=CC=1>[CH2:17]([C:14]1[S:33][C:11]([C:8]2[S:7][C:6]([Sn:5]([CH2:27][CH2:28][CH2:29][CH3:30])([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:1][CH2:2][CH2:3][CH3:4])=[CH:10][CH:9]=2)=[CH:12][CH:13]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 2

HCID 184532,5-DibromothiopheneHCID 12067697Tributyl[5-(4-hexylphenyl)-2-thienyl]stannane

Product 1

HCID 10744982Stannane, tributyl(5'-hexyl[2,2'-bithiophen]-5-yl)-

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

5′,2″:5″,2′″:5′″,2″″-pentathiophene (6TTTTT6) is now discussed. The compound 5′-hexyl-5-tributylstannylbithiophene is prepared from 2′-hexylbithiophene using the procedure described for 2-(tri-n-butylstannyl)-5-(4-n-hexylphenyl)thiophene. A measured 6.25 mmol of this compound, 2.5 mmol of 2,5-dibromothiophene, 145 mg of tetrakis(triphenylphosphine)palladium, and 35 mL of toluene are heated just below reflux for three days under nitrogen. The precipitate is successively washed with dilute hydrochloric acid, water, and acetone, and recrystallized from mesitylene with hot filtration.

Workup

  1. temperaturebelow reflux for three days under nitrogen
  2. washThe precipitate is successively washed with dilute hydrochloric acid, water, and acetone
  3. customrecrystallized from mesitylene with hot filtration

Sources & evidence

ORD record
ord-d625669b52c2427bbb4be366cac971f5
Source dataset
uspto-grants-2013_05
Patent number
US08450723B2

Reaction notes

Loading…