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

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

Reactant 4

HCID 6547Azobisisobutyronitrile

HCID 67184N-bromobutanimide

HCID 3127335-Methylthiophene-2-carbonitrile

HCID 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].