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

HRID 531173

反応式

HRID 531173 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-e98d1b91c944432081324df92623e01c
出典データセット
uspto-grants-2016_05
特許番号
US09353125B2

関連ノート

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