Benzoyl Peroxide → HCID 18986082, compound

HRID 244470Notes

Reaction equation

HRID 244470 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[CH:3]=1.[Br:9]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][Br:9])[CH:3]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 27628354-Bromo-2-methylpyridine

Product 1

HCID 18986082HCID 18986082, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred room temperature solution of 4-bromo-2-methylpyridine (1.72 g, 10 mmol) in carbon tetrachloride at was added N-bromosuccinimide (1.9 g, 10.5 mmol). The mixture was warmed at 90° C. After 30 minutes, the mixture was cooled, and benzoyl peroxide (100 mg) was added and refluxing was continued. After 7 hours, the mixture was cooled to room temperature, washed with aqueous sodium bicarbonate, brine, dried over anhydrous sodium sulfate, and concentrated in vacuo to afford 4-bromo-2-bromomethylpyridine as a brown oil [MS m/z 250/252/254 (MH+)] which was determined to be 75% pure and was used without further purification. The remaining material was determined to be 4-bromo-2-dibromomethylpyridine.

Workup

  1. temperaturethe mixture was cooled
  2. temperaturerefluxing
  3. waitAfter 7 hours
  4. temperaturethe mixture was cooled to room temperature
  5. washwashed with aqueous sodium bicarbonate, brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c098a98aac284dd98acae8f8b8e95b49
Source dataset
uspto-grants-2014_02
Patent number
US08658637B2

Reaction notes

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