N-bromobutanimide → 5-Bromo-[2,2']bithiophenyl

HRID 1738403Notes

Reaction equation

HRID 1738403 reaction equation
[Br:1]N1C(=O)CCC1=O.[S:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:14]1[S:15][CH:16]=[CH:17][CH:18]=1>C(O)(=O)C.C(Cl)(Cl)Cl>[Br:1][C:13]1[S:9][C:10]([C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 681202,2'-Bithiophene

Product 1

HCID 6400655-Bromo-[2,2']bithiophenylYield 88%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

N-Bromosuccinimide (NBS, 1.12 g, 6.3 mmol) was added in small portions to a stirred solution of 1.0 g {6.01 mmol} of 2,2'-bithiophene in 10 ml of glacial acetic acid and 10 ml of chloroform. After stirring for 1 h at room temperature, the mixture was poured into ice-water and extracted into chloroform (75 ml). The organic layer was washed with aqueous sodium bicarbonate solution, water, and then dried over magnesium sulfate and evaporated. The residue was subjected to flash chromatography on silica gel using hexane to give 1.3 g (88%) of a light green solid, m.p. 55-56° C.

Workup

  1. extractionextracted into chloroform (75 ml)
  2. washThe organic layer was washed with aqueous sodium bicarbonate solution, water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-28f7379192de460ab3d632361f9c75f3
Source dataset
uspto-grants-1999_10
Patent number
US05962490

Reaction notes

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