8-Methylquinoline → 8-(Bromomethyl)quinoline

HRID 2041232Notes

Reaction equation

HRID 2041232 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.C1C(=O)N([Br:19])C(=O)C1>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[Br:19][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2

Participants

5

Reactant 2

HCID 119108-MethylquinolineHCID 67184N-bromobutanimide

Product 1

HCID 3469148-(Bromomethyl)quinolineYield 83.7%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

Combine 8-methyl-quinoline (1.0 g, 6.99 mmol), NBS (1.3 g, 7.13 mmol), benzoyl peroxide (6.0 mg, 0.03 mmol), carbon tetrachloride (30 mL) and reflux for 17 h. Cool the reaction mixture to ambient temperature and evaporate the solvent. Dissolve the residue in chloroform (30 mL), wash the organic solution with saturated aqueous NaHCO3 (2×10 mL), brine (10 mL) and dry over anhydrous Na2SO4. Evaporate the solvent and purify by chromatography on silica gel eluting with DCM to obtain the title compound as a white solid (1.3 g, 83%). MS (ES+) m/z: 223 (M+H)+.

Workup

  1. customevaporate the solvent
  2. dissolutionDissolve the residue in chloroform (30 mL)
  3. washwash the organic solution with saturated aqueous NaHCO3 (2×10 mL), brine (10 mL)
  4. dry with materialdry over anhydrous Na2SO4
  5. customEvaporate the solvent
  6. custompurify by chromatography on silica gel eluting with DCM

Sources & evidence

ORD record
ord-f914b64b5b6c44ddb836214348aa54f3
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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