6-Methylquinoline → 6-(Bromomethyl)quinoline

HRID 74814Notes

Reaction equation

HRID 74814 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:12][CH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 70596-MethylquinolineHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimide

Product 1

HCID 2243966-(Bromomethyl)quinoline

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 6-methylquinoline (5 g, 35 mmol, 1 eq.), N-Bromosuccinimide (8.1 g, 45.5 mmol, 1.3 eq.) and benzoyl peroxide (840 mg, 3.5 mmol, 0.1 eq.) in carbon tetrachloride (100 mL) was stirred at reflux for 3 hours and then cooled to room temperature. The reaction mixture was filtered and the filtrate was concentrated in vacuo. The residue was dissolved in tetrahydrofuran (100 mL) and filtered. The filtrate was directly used in the next step without further purification

Workup

  1. temperatureat reflux for 3 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. dissolutionThe residue was dissolved in tetrahydrofuran (100 mL)
  5. filtrationfiltered
  6. customThe filtrate was directly used in the next step without further purification

Sources & evidence

ORD record
ord-8c9af432ee0e4b06b9c7fc4fd393edbc
Source dataset
uspto-grants-2014_09
Patent number
US08828401B2

Reaction notes

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