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

HRID 531172

반응식

HRID 531172 반응식
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

참가 물질

4

반응물 2

HCID 6263614,7-Dibromo-2,1,3-benzothiadiazole2회HCID 27793732-(Tri-n-butylstannyl)thiophene

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-6e424d0149d0477ca912322c0c27592f
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09353125B2

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