反应详情

温度

95 °C

To a solution of methyl 4-bromo-2-methylbenzoate (6.9 g) in 1,4-dioxane (150 ml) was added bis(pinacolato)diboron (8.03 g), dichlorobis(triphenylphosphine)palladium(II) (1.69 g) and potassium acetate (8.87 g), and the mixture was stirred at 95° C. for 2 hours under nitrogen. The mixture was diluted with ethyl acetate and water. The organic layer was separated, washed with 1N hydrochloric acid and brine, dried over magnesium sulfate and evaporated. To a suspension of the crude product (11 g) in acetone (200 ml) and water (200 ml) was added ammonium acetate (5.1 g) and sodium periodate (14.1 g), and the mixture was stirred at room temperature for 6 hours. The solvent was evaporated, and the mixture was diluted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over magnesium sulfate and evaporated under reduced pressure. The resultant solid was triturated with diisopropyl ether to give [3-methyl-4-(methoxycarbonyl)phenyl]boronic acid (2.65 g).

1. customThe organic layer was separated
2. washwashed with 1N hydrochloric acid and brine
3. dry with materialdried over magnesium sulfate
4. customevaporated
5. additionTo a suspension of the crude product (11 g) in acetone (200 ml) and water (200 ml)
6. additionwas added ammonium acetate (5.1 g) and sodium periodate (14.1 g)
7. stirringthe mixture was stirred at room temperature for 6 hours
8. customThe solvent was evaporated
9. additionthe mixture was diluted with ethyl acetate
10. customThe organic layer was separated
11. washwashed with water and brine
12. dry with materialdried over magnesium sulfate
13. customevaporated under reduced pressure
14. customThe resultant solid was triturated with diisopropyl ether