Reaction #2439926

Reaction equation

2-(p-fluorophenyl)-4-methyl-pyridine

N-bromosuccinimide

benzoylperoxide

→

2-(p-fluorophenyl)-4-bromomethyl-pyridine

Yield 88.7%

Solvents

CCl4

Conditions

Workup

1. 1
   Temperatureat reflux temperature
2. 2
   Otherirradiated by means of an ordinary 250-W UV lamp for 4 hrs
3. 3
   TemperatureAfterwards, the reaction mixture was cooled
4. 4
   Othersubsequently triturated with Et2O/petroleum benzine
5. 5
   OtherThe precipitate was removed by filtration
6. 6
   Concentrationthe filtrate was concentrated in vacuo

Procedure

A mixture of 2-(p-fluorophenyl)-4-methyl-pyridine (0.5 g, 2.67 mmol), N-bromosuccinimide (0.48 g, 2.69 mmol), and a catalytic amount of benzoylperoxide in CCl4 (50 ml) was stirred at reflux temperature and irradiated by means of an ordinary 250-W UV lamp for 4 hrs. Afterwards, the reaction mixture was cooled and subsequently triturated with Et2O/petroleum benzine. The precipitate was removed by filtration, and the filtrate was concentrated in vacuo to give 2-(p-fluorophenyl)-4-bromomethyl-pyridine (0.63 g, 88%, unstable) as a dark yellow oil.

Source