N-bromobutanimide → 2-Bromo-5-bromomethylpyridine

HRID 1175622Notes

Reaction equation

HRID 1175622 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.[Br:9]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][Br:9])=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 5642162-Bromo-5-methylpyridine

Product 1

HCID 64246602-Bromo-5-bromomethylpyridineYield 82.5%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-bromo-5-methylpyridine (5 g, 29 mmol) in carbon tetrachloride (50 mL) was added N-bromosuccinimide (7.79 g, 44 mmol). The mixture was heated to 80° C., then dibenzoyl peroxide (53 mg, 0.22 mmol) was added and the mixture was stirred at 80° C. for 4 h then cooled to room temperature, washed with water and brine, dried over Na2SO4, filtered and evaporated. The residue was chromatographed on silica gel (30% EtOAc/heaxanes) to give 6 g of 2-Bromo-5-(bromomethyl)pyridine (MS+H, 251.8).

Workup

  1. temperaturethen cooled to room temperature
  2. washwashed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was chromatographed on silica gel (30% EtOAc/heaxanes)

Sources & evidence

ORD record
ord-33b60d65cc384336bc0f8f86cf6ad7ee
Source dataset
uspto-grants-2010_11
Patent number
US07842324B2

Reaction notes

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