Benzoyl Peroxide → 2-(1-Bromoethyl)pyridine

HRID 911773Notes

Reaction equation

HRID 911773 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-fb7db44782ab43e5a2605f0c5b6ac47d
Source dataset
uspto-grants-2011_09
Patent number
US08022223B2

Reaction notes

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