Реакция #43920

Уравнение реакции

sodium thiosulfate

4-bromo-3,5-dimethylphenol

N-fluoropyridinium triflate

→

title compound

Выход 36.2%

4-bromo-2-fluoro-3,5-dimethylphenol

Выход 36.2%

Растворители

1,2-dichloroethane

Условия реакции

Обработка

1. 1
   Температураthe mixture was heated
2. 2
   Температураunder reflux for 7 hr
3. 3
   Экстракцияextracted with ethyl acetate
4. 4
   ПромывкаThe extract was washed successively with water and saturated brine
5. 5
   Сушкаdried over anhydrous magnesium sulfate
6. 6
   Концентрированиеconcentrated under reduced pressure
7. 7
   ДругоеThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-30:70)

Методика

To a solution of 4-bromo-3,5-dimethylphenol (2.00 g, 9.95 mmol) in 1,2-dichloroethane (20 mL) was added N-fluoropyridinium triflate (6.15 g, 24.9 mmol), and the mixture was heated under reflux for 7 hr. The reaction mixture was treated with 1 M aqueous sodium thiosulfate solution, and extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-30:70) to give the title compound (0.790 g, yield 36%) as a colorless oil.

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