Benzoyl Peroxide → 2-(1-Bromoethyl)pyridine
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
Product 1
Reagents, catalysts & solvents 1
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
- temperatureThe reaction mixture was heated
- temperatureto reflux for 18 hours
- filtrationfiltered
- concentrationThe filtrate was concentrated
- customthe residue was purified over a plug of silica
Sources & evidence
- ORD record
- ord-b6cd741540ee4b83a966361d0022c63f
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08883828B2
Reaction notes
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