Benzoyl Peroxide → 2-(Bromomethyl)-6-fluoroquinoline

HRID 1655969Notes

Reaction equation

HRID 1655969 reaction equation
[F: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.[Br:13]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:13][CH2:12][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([F:1])[CH:3]=2)[N:8]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 707846-Fluoro-2-methylquinoline

Product 1

HCID 216180422-(Bromomethyl)-6-fluoroquinoline

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 6-fluoro-2-methylquinoline (see C. M. Leir, J. Org. Chem., vol 42, pp 911-913, 1977) (21.67 g) in carbon tetrachloride (700 mL) were added N-bromosuccinimide (26.32 g) and benzoyl peroxide (1.62 g). The mixture was brought to reflux with two spot lights of 150 Watts. The mixture was irradiated for 24 hours at reflux. The mixture was then cooled to room temperature, evaporated to dryness and chromatographed on flash silica gel using pure toluene as eluant to give, as the slower running compound, a beige solid (11.9 g); m.p. 90°-92° C.

Workup

  1. temperatureto reflux with two spot lights of 150 Watts
  2. customThe mixture was irradiated for 24 hours
  3. temperatureat reflux
  4. customevaporated to dryness
  5. customchromatographed on flash silica gel using pure toluene as eluant
  6. customto give

Sources & evidence

ORD record
ord-82dc54d8fa9d4eb0b90c43bd50129636
Source dataset
uspto-grants-1993_10
Patent number
US05252585

Reaction notes

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