Azobisisobutyronitrile → 5-(Bromomethyl)thiophene-2-carbonitrile

HRID 1506140Notes

Reaction equation

HRID 1506140 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7]#[N:8])=[CH:4][CH:3]=1.[Br:9]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)(Cl)Cl>[Br:9][CH2:1][C:2]1[S:6][C:5]([C:7]#[N:8])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 24477Sodium ThiosulfateHCID 67184N-bromobutanimideHCID 3127335-Methylthiophene-2-carbonitrile

Product 1

HCID 105600165-(Bromomethyl)thiophene-2-carbonitrileYield 23%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

5-Methylthiophene-2-carbonitrile (500 mg, 4.06 mmol) in carbon tetrachloride (10 mL) was stirred with N-bromosuccinimide (867 mg, 4.87 mmol) and 2,2′-azobis(isobutyronitrile) (133 mg, 0.810 mmol) at 60° C. for 4.5 hours and allowed to cool to room temperature. After addition of saturated aqueous sodium thiosulfate, the reaction mixture was extracted with chloroform, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1␣1/1 (v/v)) to give the title compound as a yellow oil (186 mg, yield 23%).

Workup

  1. extractionthe reaction mixture was extracted with chloroform
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1␣1/1 (v/v))

Sources & evidence

ORD record
ord-9f810e49c35f4ddbac347925a7530607
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

Loading…