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

HRID 531173

반응식

HRID 531173 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-benzothiadiazoleHCID 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

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-e98d1b91c944432081324df92623e01c
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09353125B2

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