Azobisisobutyronitrile → 7-(Bromomethyl)-2-chloro-4-(4-fluorophenyl)quinoline

HRID 2422550Notes

Reaction equation

HRID 2422550 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][C:6]([CH3:19])=[CH:7][CH:8]=2)[N:3]=1.[Br:20]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:20][CH2:19][C:6]1[CH:5]=[C:4]2[C:9]([C:10]([C:12]3[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=3)=[CH:11][C:2]([Cl:1])=[N:3]2)=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 866219782-Chloro-4-(4-fluorophenyl)-7-methylquinoline

Product 1

HCID 866219797-(Bromomethyl)-2-chloro-4-(4-fluorophenyl)quinoline

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 2-chloro-4-(4-fluorophenyl)-7-methylquinoline (2.0 g, 7.4 mmol), N-bromo-succinimide (1.57 g, 8.8 mmol) and AIBN (30 mg, 0.18 mmol) in CCl4 (40 mL) was refluxed for 16 h. The solution was then cooled to rt, filtered and concentrated. Purification on silica gel (eluting with dichloromethane/hexanes, 1:1) gave the title compound. MS (+ESI): 351 (M+H)+.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customPurification on silica gel (eluting with dichloromethane/hexanes, 1:1)

Sources & evidence

ORD record
ord-9238ea38c98849b290a508295201496e
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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