N-bromobutanimide → 2-Bromo-5-propylthiophene

HRID 1774586Notes

Reaction equation

HRID 1774586 reaction equation
[CH2:1]([C:4]1[S:5][CH:6]=[CH:7][CH:8]=1)[CH2:2][CH3:3].[Br:9]N1C(=O)CCC1=O>CN(C)C=O>[Br:9][C:6]1[S:5][C:4]([CH2:1][CH2:2][CH3:3])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 737712-Propylthiophene

Product 1

HCID 218019042-Bromo-5-propylthiopheneYield 89.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-propylthiophene (1.00 g, 7.92 mmol) and N-bromosuccinimide (1.55 mg, 8.71 mmol) in N,N-Dimethylformamide (60 mL) was heated at 65° C. for 4 hours. The reaction mixture was concentrated in vacuo. The residue was dissolved in cyclohexane (20 mL) and successively washed with a 5% sodium thiosulfate solution (15 mL) and brine (15 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo to provide 2-bromo-5-propylthiophene (11a) (1.45 g, 7.07 mmol, 89%) which was used without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in cyclohexane (20 mL)
  3. washsuccessively washed with a 5% sodium thiosulfate solution (15 mL) and brine (15 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b39fcc1caa8d4700bcf00c9c2c4027bf
Source dataset
uspto-grants-2016_02
Patent number
US09260395B2

Reaction notes

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