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

HRID 531172

反応式

HRID 531172 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-benzothiadiazole2 回HCID 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

According to what is described by Kitamura et al. in “Chemistry of Material” (1996), Vol. 8, pages 570-578, for example, 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, in a quantity equal to 2 moles per 100 moles of 4,7-dibromo-2,1,3-benzothiadiazole. 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 82%.

後処理

  1. customcan be prepared
  2. customAt 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-6e424d0149d0477ca912322c0c27592f
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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