Réaction #539827

Équation de réaction

trimethylsilylazide hexane

3-chloro-4-(dihydroxyboryl)benzoic acid

N,N-dimethylformamide

diethyl ether

→

title compound

Rendement 42.0%

[2-chloro-4-(methoxycarbonyl)phenyl]boronic acid

Rendement 42.0%

Solvants

Acetic acid

Conditions de réaction

Traitement

1. 1
   Concentrationthe mixture was concentrated under reduced pressure
2. 2
   workup.ADDITIONWater was added to the residue
3. 3
   Filtrationthe precipitate was collected by filtration
4. 4
   Autrerecrystallized from water

Mode opératoire

To a mixture of 3-chloro-4-(dihydroxyboryl)benzoic acid (1.00 g, 5.10 mmol), N,N-dimethylformamide (10 mL) and diethyl ether (1 ml) was added dropwise a 0.6 M trimethylsilylazide-hexane solution (10.2 mL, 6.12 mmol), and the resulting mixture was stirred overnight at room temperature. Acetic acid was added to the reaction mixture, and the mixture was concentrated under reduced pressure. Water was added to the residue, and the precipitate was collected by filtration and recrystallized from water to give the title compound (0.46 g, yield 42%) as colorless crystals.

Source