反応 #1183738

反応方程式

6-chloro-5-fluoro-3-methylpyridine

N-chlorosuccinimide

N-chlorosuccinimide

2,2′-azobis(2-methylpropannitrile)

2,2′-azobis(2-methylpropannitrile)

→

6-chloro-3-chloromethyl-5-fluoropyridine

収率 53.0%

溶媒

chlorobenzene

反応条件

後処理

1. 1
   温度under reflux for 2 days
2. 2
   その他During this reaction
3. 3
   洗浄The reaction mixture is washed with saturated aqueous sodium sulphite solution and sodium bicarbonate solution
4. 4
   乾燥dried over sodium sulphite
5. 5
   濃縮concentrated under reduced pressure

実験手順

1.00 g (6.87 mmol) of 6-chloro-5-fluoro-3-methylpyridine (F. L. Setliff, Organic Preparations and Procedures International 1971, 3, 217-222), 1.01 g (7.56 mmol) of N-chlorosuccinimide and 0.11 g (0.69 mmol) of 2,2′-azobis(2-methylpropannitrile) in 100 ml of chlorobenzene are boiled under reflux for 2 days. During this reaction, after about 16 hours and 32 hours, a further 1.01 g (7.56 mmol) of N-chlorosuccinimide and 0.11 g (0.69 mmol) of 2,2′-azobis(2-methylpropannitrile) are added in each case. The reaction mixture is washed with saturated aqueous sodium sulphite solution and sodium bicarbonate solution and then dried over sodium sulphite and concentrated under reduced pressure. Column chromatography of the residue on silica gel (silica gel 60-Merck, particle size: 0.04 to 0.063 mm) using the mobile phase mixture ethyl acetate:cyclohexane (1:20) gives 0.65 g (53% of theory) of 6-chloro-3-chloromethyl-5-fluoropyridine.

出典