N-bromobutanimide → 2-Bromo-5-butylsulphanylthiophene

HRID 1901396Notes

Reaction equation

HRID 1901396 reaction equation
[CH2:1]([S:5][C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4].[Br:11]N1C(=O)CCC1=O>C(Cl)(Cl)Cl.C(O)(=O)C.O>[Br:11][C:8]1[S:7][C:6]([S:5][CH2:1][CH2:2][CH2:3][CH3:4])=[CH:10][CH:9]=1

Participants

6

Reactant 2

HCID 67184N-bromobutanimideHCID 520967Thiophene, 2-(butylthio)-

Product 1

HCID 233673822-Bromo-5-butylsulphanylthiophene

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

A solution of compound 6 (5.18 g, 0.030 mol) and N-bromosuccinimide (5.34 g, 0.030 mol) in chloroform (80 ml) and glacial acetic acid (80 ml) was gently heated under reflux (with stirring) for 0.5 h (glc analysis revealed a complete reaction). The reaction mixture was diluted with water and washed with dichloromethane (2×100 ml); the combined organic extracts were washed successively with water (300 ml) and aqueous potassium hydroxide (5%, 300 ml) before being dried (MgSO4). The solvent was removed in vacuo and the residue was distilled to give a colourless liquid.

Workup

  1. temperatureunder reflux
  2. customa complete reaction)
  3. washwashed with dichloromethane (2×100 ml)
  4. washthe combined organic extracts were washed successively with water (300 ml) and aqueous potassium hydroxide (5%, 300 ml)
  5. dry with materialbefore being dried (MgSO4)
  6. customThe solvent was removed in vacuo
  7. distillationthe residue was distilled
  8. customto give a colourless liquid

Sources & evidence

ORD record
ord-84bd976cfbe444a1aba39a08804a0629
Source dataset
uspto-grants-1996_11
Patent number
US05578242

Reaction notes

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