Water → 2-Bromo-3-phenylthiophene

HRID 1275731Notes

Reaction equation

HRID 1275731 reaction equation
[C:1]1([C:7]2[CH:11]=[CH:10][S:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C(=O)N([Br:19])C(=O)C1.O>C(Cl)(Cl)Cl.CC(O)=O>[Br:19][C:8]1[S:9][CH:10]=[CH:11][C:7]=1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 754733-Phenylthiophene

Product 1

HCID 217668842-Bromo-3-phenylthiopheneYield 78.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

3-Phenylthiophene (0.58 g, 3.62 mmol) was dissolved in 15 mL of a 1:1 solution of CHCl3 and AcOH followed by the portion-wise addition of 0.77 g (4.3 mmol) of NBS. The mixture was stirred at room temperature for 1 h, poured into 25 mL of H2O, and diluted with 30 mL of hexanes. The organic layer was washed successively with 2×10 mL of 10% aqueous KOH solution, 2×10 mL of H2O, and 2×10 mL of brine, and concentrated in vacuo to provide 0.68 g (78% yield) of 2-bromo-3-phenylthiophene as an oil.

Workup

  1. washThe organic layer was washed successively with 2×10 mL of 10% aqueous KOH solution, 2×10 mL of H2O, and 2×10 mL of brine
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-428cb83a711146089d8389a83379de3b
Source dataset
uspto-grants-2000_12
Patent number
US06162824

Reaction notes

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