Azobisisobutyronitrile → 5-Bromo-2-(bromomethyl)benzo[b]thiophene

HRID 330283

Reaction equation

HRID 330283 reaction equation
[Br:1]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.[Br:21][C:22]1[CH:23]=[CH:24][C:25]2[S:29][C:28]([CH3:30])=[CH:27][C:26]=2[CH:31]=1>C(Cl)(Cl)(Cl)Cl>[Br:1][CH2:30][C:28]1[S:29][C:25]2[CH:24]=[CH:23][C:22]([Br:21])=[CH:31][C:26]=2[CH:27]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 136630355-Bromo-2-methyl-1-benzothiophene

Product 1

HCID 148193525-Bromo-2-(bromomethyl)benzo[b]thiopheneYield 90.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Conditions

Temperature
0 °C

Procedure

According to the procedure of S. Gronowitz, et al., Synth. Commin., 6, (7), 475 (1976), to a stirred, boiling partial solution of N-bromosuccinimide (17.63 g, 0.099 mol) in CCl4 (200 mL) was added 2,2'-azobis-(2-methylpropionitrile) (1.1 g, 0.007 mol). After one minute, a solution of 5-bromo-2-methylbenzthiophene (15.0 g, 0.066 mol) in CCl4 (100 mL) was added. The resulting mixture was heated at reflux for 2 hours and cooled to 0° C. The solid was filtered. The filtrate was concentrated to give 18.19 g (90%) of product as an orange solid.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 2 hours
  3. filtrationThe solid was filtered
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-b90f1f9bb09e477b8e1100f37d3a4b81
Source dataset
uspto-grants-1990_01
Patent number
US04895860

Linked notes

Loading…