Benzoyl Peroxide → 2-(1-Bromoethyl)pyridine

HRID 335084

Reaction equation

HRID 335084 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)[CH3:2].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Br:27]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:27][CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 75232-EthylpyridineHCID 67184N-bromobutanimide

Product 1

HCID 153736572-(1-Bromoethyl)pyridineYield 49.9%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

2-Ethylpyridine (20.0 g, 186.65 mmol) was placed in carbon tetrachloride (830 mL) and benzoyl peroxide (4.5211 g, 18.665 mmol) and 1-bromopyrrolidine-2,5-dione (33.221 g, 186.65 mmol) were added. The reaction mixture was heated to reflux for 18 hours, then cooled to room temperature and filtered. The filtrate was concentrated and the residue was purified over a plug of silica to give 2-(1-bromoethyl)pyridine (17.312 g, 49.9%). 1H NMR (CDCl3) δ 8.58 (d, 1H), 7.69 (td, 1H), 7.76 (d, 1H), 7.20 (dd, 1H), 5.24 (q, 1H), 2.08 (d, 3H)

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 18 hours
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified over a plug of silica

Sources & evidence

ORD record
ord-b6cd741540ee4b83a966361d0022c63f
Source dataset
uspto-grants-2014_11
Patent number
US08883828B2

Linked notes

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