4,7-Dibromo-2,1,3-benzothiadiazole → 4,7-Di(thiophen-2-yl)benzo(c)(1,2,5)thiadiazole

HRID 531173

Reaction equation

HRID 531173 reaction equation
Br[C:2]1[C:10]2[C:6](=[N:7][S:8][N:9]=2)[C:5](Br)=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:17]1[S:18][CH:19]=[CH:20][CH:21]=1)CCC>O1CCCC1>[S:18]1[CH:19]=[CH:20][CH:21]=[C:17]1[C:2]1[C:10]2[C:6](=[N:7][S:8][N:9]=2)[C:5]([C:19]2[S:18][CH:17]=[CH:21][CH:20]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6263614,7-Dibromo-2,1,3-benzothiadiazoleHCID 27793732-(Tri-n-butylstannyl)thiophene

Product 1

HCID 3962944,7-Di(thiophen-2-yl)benzo(c)(1,2,5)thiadiazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

An analogous process is described by Kim et al. in “Journal of Material Chemistry” (2008), Vol. 18, pages 5223-5229, in which 4,7-di-2-thienyl-2,1,3-benzothia-diazole (DTB) can be prepared by reacting 4,7-dibromo -2,1,3-benzothiadiazole and tri-n-butyl(thien-2-yl)stannane, in the presence of tetrahydrofuran, at 66° C., for 3 hours. Bis(triphenylphosphine)palladium-(II)chloride [PdCl2(PPh3)2] is used as catalyst. Also in this case, at the end of the reaction, the solvent is removed by evaporation at reduced pressure and the residue obtained is purified by elution on a silica gel chromatographic column using a mixture of methylene chloride/hexane (1/1 vol/vol) as eluent, obtaining 4,7-di-2-thienyl-2,1,3-benzothiadiazole (DTB) with a yield equal to 88%.

Workup

  1. customcan be prepared
  2. customAlso in this case, at the end of the reaction
  3. customthe solvent is removed by evaporation at reduced pressure
  4. customthe residue obtained
  5. customis purified by elution on a silica gel chromatographic column
  6. additiona mixture of methylene chloride/hexane (1/1 vol/vol) as eluent

Sources & evidence

ORD record
ord-e98d1b91c944432081324df92623e01c
Source dataset
uspto-grants-2016_05
Patent number
US09353125B2

Linked notes

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