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

HRID 2270587Notes

Reaction equation

HRID 2270587 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 88.2%

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-c0623b089e4046afb2feae61cdb1745a
Source dataset
uspto-grants-2001_12
Patent number
US06331637B1

Reaction notes

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