Benzoyl Peroxide → 6-Bromo-2-(chloromethyl)quinoline

HRID 2075678Notes

Reaction equation

HRID 2075678 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[CH:6]=[CH:5]2.C1C(=O)N([Cl:20])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH2:12][Cl:20])[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 31398ChlorosuccinimideHCID 5228856-Bromo-2-methylquinoline

Product 1

HCID 582577966-Bromo-2-(chloromethyl)quinoline

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
80 °C

Procedure

To 6-Bromo-2-methyl-quinoline (2.4 g, 11.0 mmol) in benzene (20 mL) at room temperature was added NCS (1.44 g, 11.0 mmol) and catalytic benzoyl peroxide, and the reaction was heated to 80° C. for 1 hour. After cooling to room temperature, the mixture was concentrated and purified by silica gel chromatography (0-50% EtOAc in hexanes) to give the desired product, 4a.

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe mixture was concentrated
  3. custompurified by silica gel chromatography (0-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d9a17cd1293c4f3ea798c23339687cf7
Source dataset
uspto-grants-2011_04
Patent number
US07919621B2

Reaction notes

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