N-bromobutanimide → 3-(Bromomethyl)-2,5-dichlorothiophene

HRID 1004168Notes

Reaction equation

HRID 1004168 reaction equation
[Cl:1][C:2]1[S:3][C:4]([Cl:8])=[CH:5][C:6]=1[CH3:7].[Br:9]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:9][CH2:7][C:6]1[CH:5]=[C:4]([Cl:8])[S:3][C:2]=1[Cl:1]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 2689102,5-Dichloro-3-methylthiophene

Product 1

HCID 234340823-(Bromomethyl)-2,5-dichlorothiopheneYield 91.1%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a stirred solution of 2,5-dichloro-3-methylthiophene (25.8 g, 154 mmol) in carbon tetrachloride (47 mL) was added N-bromosuccinimide (27.5 g, 154 mmol) and benzoyl peroxide (310 mg, 1.28 mmol). The mixture was heated at reflux temperature for 8 hours. After cooling, the insolubles were filtered off. The filtrate was washed with aqueous sodium sulfite solution, dried over MgSO4, and concentrated in vacuo. The residue was fractionally distilled under reduced pressure (bp 80° C., 0.5 mmHg) to give the subtitle compound (34.5 g, 91% yield).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux temperature for 8 hours
  3. temperatureAfter cooling
  4. filtrationthe insolubles were filtered off
  5. washThe filtrate was washed with aqueous sodium sulfite solution
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. distillationThe residue was fractionally distilled under reduced pressure (bp 80° C., 0.5 mmHg)

Sources & evidence

ORD record
ord-0bdfe2261e10431a8fe862dfc87a5c9b
Source dataset
uspto-grants-2000_04
Patent number
US06048880

Reaction notes

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