N-bromobutanimide → Quinoline, 6-(bromomethyl)-2-chloro-

HRID 1432849Notes

Reaction equation

HRID 1432849 reaction equation
[Br:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH3:20])[CH:16]=2)[N:11]=1>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:1][CH2:20][C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[N:11]=[C:10]([Cl:9])[CH:19]=[CH:18]2

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 779742-Chloro-6-methylquinoline

Product 1

HCID 11276889Quinoline, 6-(bromomethyl)-2-chloro-Yield 50.8%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

N-Bromosuccinimide (12.9 g, 72.5 mmol) and benzoyl peroxide (0.33 g, 1.30 mmol) are added to a solution of 2-chloro-6-methyl-quinoline (12.0 g, 67.5 mmol) in carbon tetrachloride (300 mL). The mixture is heated at reflux for 6 hours. At this time, the resulting mixture is cooled to room temperature, filtered, washed with CH2Cl2 and concentrated in vacuo. The crude residue is recrystallized from 50% EtOAc/hexanes to yield the title compound (8.80 g, 34.3 mmol) as a beige crystalline solid. 1H NMR (CDCl3, 300 MHz) δ8.08 (d, 1H), 8.02 (d, 1H), 7.83 (s, 1H), 7.77 (dd, 1H), 7.40 (d, 1H), 4.65 (s, 2H). MS (EI): m/z 256, 258 (M+), Cl pattern.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 6 hours
  3. filtrationfiltered
  4. washwashed with CH2Cl2
  5. concentrationconcentrated in vacuo
  6. customThe crude residue is recrystallized from 50% EtOAc/hexanes

Sources & evidence

ORD record
ord-f550c8a738634ce589115184b47fb006
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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