Реакция #1961

Уравнение реакции

AIBN

4-Chloro-5-fluoro-2-picoline

product

4-Chloro-5-fluoro-2-picoline

N-bromosuccinimide

→

title compound

Выход 69.0%

4-Chloro-5-fluoro-alpha-bromo-2-picoline

Выход 69.0%

Растворители

methylene chloride

1,2-dichloroethane

Условия реакции

Обработка

1. 1
   workup.STIRRINGAfter the reaction mixture was stirred at 75° C. for 24 hours
2. 2
   Промывкаwashed with 3 X 400 mL of water
3. 3
   ДругоеThe organic layer was separated
4. 4
   Сушкаdried over anhydrous sodium sulfate
5. 5
   Фильтрацияfiltered
6. 6
   Концентрированиеconcentrated under reduced pressure
7. 7
   ДругоеThe residue was dried in vacuo

Методика

4-Chloro-5-fluoro-2-picoline (2.9 g, 20 mmol), the product of Example 66, was dissolved in 50 mL of 1,2-dichloroethane in a dry flask. The resultant solution was heated, with stirring, to 75° C. and 4.09 (23 mmol) of N-bromosuccinimide was added, followed by 100 mG (0.7 mmol) of 2,2-azobisisobutyronirile (AIBN), a free radical initiator. After the reaction mixture was stirred at 75° C. for 24 hours, it was diluted with 450 mL of methylene chloride and washed with 3 X 400 mL of water. The organic layer was separated and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was dried in vacuo to give 3.5 g (69% yield) of the title compound as an amber oil; 1H NMR (CDCl3) d 4.50 (s, 2H), 7.54 (d, 1H), 8.44 (s, 1H).

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