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

HRID 1899621Notes

Reaction equation

HRID 1899621 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 10ml 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-50d21feebc324576bb9978547ea0d024
Source dataset
uspto-grants-1996_11
Patent number
US05571821

Reaction notes

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