Azobisisobutyronitrile → 5-Bromomethyl-3-chloro-2-(2-trifluoromethyl-biphenyl-4-yl)-benzo[b]thiophene

HRID 2353371Notes

Reaction equation

HRID 2353371 reaction equation
[Cl:1][C:2]1[C:3]2[CH:26]=[C:25]([CH3:27])[CH:24]=[CH:23][C:4]=2[S:5][C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:9]([C:19]([F:22])([F:21])[F:20])[CH:8]=1.C1C(=O)N([Br:35])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:35][CH2:27][C:25]1[CH:24]=[CH:23][C:4]2[S:5][C:6]([C:7]3[CH:12]=[CH:11][C:10]([C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=4)=[C:9]([C:19]([F:22])([F:21])[F:20])[CH:8]=3)=[C:2]([Cl:1])[C:3]=2[CH:26]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 68453943HCID 68453943, compound

Product 1

HCID 684526035-Bromomethyl-3-chloro-2-(2-trifluoromethyl-biphenyl-4-yl)-benzo[b]thiopheneYield 38%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 3-chloro-5-methyl-2-(2-trifluoromethyl-biphenyl-4-yl)-benzo[b]thiophene (110 mg, 0.273 mmol) in CCl4 (3 ml) is added NBS (49 mg, 1 eq.). The mixture is heated at reflux for 15 minutes before AIBN (4.5 mg, 0.1 eq.) is added. The reaction is further heated at reflux overnight. The mixture is filtered through Celite and washed with CCl4. The filtrate is concentrated and purified by column chromatography (EtOAc/Hexane, gradient) to give 50 mg of 5-bromomethyl-3-chloro-2-(2-trifluoromethyl-biphenyl-4-yl)-benzo[b]thiophene in 38% yield.

Workup

  1. temperatureThe mixture is heated
  2. additionis added
  3. temperatureThe reaction is further heated
  4. temperatureat reflux overnight
  5. filtrationThe mixture is filtered through Celite
  6. washwashed with CCl4
  7. concentrationThe filtrate is concentrated
  8. custompurified by column chromatography (EtOAc/Hexane, gradient)

Sources & evidence

ORD record
ord-2b2885da117c4fa3a80163f65c62a989
Source dataset
uspto-grants-2010_07
Patent number
US07750021B2

Reaction notes

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