2,2':5',2''-Terthiophene → 2-Bromo-5-(5-thiophen-2-ylthiophen-2-yl)thiophene

HRID 1018017

반응식

HRID 1018017 반응식
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[S:7][C:8]([C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)=[CH:9][CH:10]=1.C1C(=O)N([Br:23])C(=O)C1>CN(C=O)C.C(Cl)Cl>[Br:23][C:13]1[S:12][C:11]([C:8]2[S:7][C:6]([C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)=[CH:10][CH:9]=2)=[CH:15][CH:14]=1

참가 물질

5

반응물 2

HCID 650672,2':5',2''-Terthiophene2회HCID 67184N-bromobutanimide

생성물 1

HCID 1853522-Bromo-5-(5-thiophen-2-ylthiophen-2-yl)thiophene수율 92%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

Using 2,2′:5′,2″-terthiophene (7, FIG. 3): N-Bromosuccimide (3.147 mg, 17.681 mmol) were added portion in portions during 5 hours to an solution of 2,2′:5′,2″-terthiophene (4.315 g, 17.373 mmol) in 10 ml DMF at −20° C. After about 90 min, a precipitate was formed. After stirring for 14 hours at room temperature, the reaction mixture was dissolved in 300 ml CH2Cl2 and washed twice with 100 ml 1N HCl. The aqueous layers were extracted with CH2Cl2 and the organic layers were dried (MgSO4) and concentrated. Purification by FC (hexanes) gave 5.222 g (56 mmol, 92%) 5-bromo-2,2′:5′,2″-terthiophene, 92%) as yellow solid.

후처리

  1. customa precipitate was formed
  2. washwashed twice with 100 ml 1N HCl
  3. extractionThe aqueous layers were extracted with CH2Cl2
  4. dry with materialthe organic layers were dried (MgSO4)
  5. concentrationconcentrated
  6. customPurification by FC (hexanes)

출처 및 근거

ORD 기록
ord-fb8f21081f5544dcb92f802efd172ed5
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06479650B1

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