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

HRID 1744409

Reaction equation

HRID 1744409 reaction equation
C1C(=O)N([Br:8])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C.[CH3:21][C:22]1[S:26][C:25]([C:27]#[N:28])=[CH:24][CH:23]=1.C1C(=O)N(Br)C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>>[Br:8][CH2:21][C:22]1[S:26][C:25]([C:27]#[N:28])=[CH:24][CH:23]=1

Participants

5

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 3127335-Methylthiophene-2-carbonitrileHCID 86630000Nbs aibn

Product 1

HCID 105600165-(Bromomethyl)thiophene-2-carbonitrile

Procedure

1.69 kg (9.51 moles) of NBS and 156 g (0.95 moles) of AIBN were well mixed and placed in a vinyl wrapper (at this time, the previous reaction was regarded to be proceeded to 100%). The benzene solution of Example 2 was heated. The NBS-AIBN mixture was portionwise added to the heated solution at 73° C. for 40 minutes. The solution was refluxed for 1.5 hours after the addition was done. After confirming completion of the reaction by HPLC, the solution was cooled to room temperature. The reaction solution was washed with [1 L of H2O+4 L of 5% NaHCO3], and then [2 L of H2O+1 L of 5% NaCl].

Workup

  1. customthe previous reaction
  2. temperatureThe solution was refluxed for 1.5 hours
  3. additionafter the addition
  4. customcompletion of the reaction by HPLC
  5. washThe reaction solution was washed with [1 L of H2O+4 L of 5% NaHCO3]

Sources & evidence

ORD record
ord-2f748aa9f05543a6be1386a4cd7d79dc
Source dataset
uspto-grants-2006_03
Patent number
US07015337B2

Linked notes

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