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

HRID 433847

Reaction equation

HRID 433847 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-8143e9f65d5e48cab30e2c53767741d4
Source dataset
uspto-grants-2003_12
Patent number
US06670193B2

Linked notes

Loading…