Реакция #59023

Уравнение реакции

Sodium metaperiodate

ethyl 3-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

hydrochloric acid

→

4-ethoxycarbonyl-2-methoxyphenylboronic acid

Выход 89.3%

Растворители

ethyl acetate

water

tetrahydrofuran

water

Условия реакции

Обработка

1. 1
   workup.STIRRINGthe mixture was stirred at that temperature for 10 min
2. 2
   workup.STIRRINGthe resulting mixture was stirred at that temperature for additional 2 hrs
3. 3
   ДругоеThe organic layer was separated
4. 4
   Промывкаwashed with water and brine
5. 5
   Сушкаdried over anhydrous magnesium sulfate
6. 6
   ДругоеThe solvent was evaporated under reduced pressure

Методика

Sodium metaperiodate (0.157 g) was added to a mixture of ethyl 3-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (0.075 g), water (1 mL) and tetrahydrofuran (4 mL) at room temperature with stirring, and the mixture was stirred at that temperature for 10 min. 2 mol/L hydrochloric acid (0.082 mL) was added, and the resulting mixture was stirred at that temperature for additional 2 hrs, then water and ethyl acetate were added. The organic layer was separated, washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to afford 4-ethoxycarbonyl-2-methoxyphenylboronic acid (0.049 g).

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