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

HRID 1018017

Reaction equation

HRID 1018017 reaction equation
[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

Participants

5

Reactant 2

HCID 650672,2':5',2''-Terthiophene2×HCID 67184N-bromobutanimide

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-fb8f21081f5544dcb92f802efd172ed5
Source dataset
uspto-grants-2002_11
Patent number
US06479650B1

Linked notes

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