Tetrahydrofuran → 2-Chloropyridine-5-boronic acid

Participants

Reaction Conditions

Reaction Steps

In a flask replaced by nitrogen, tetrahydrofuran solution (80 g) of 5-bromo-2-chloropyridine (9.6 g, 50.0 mmol) was charged, and cooled at 10° C., and then n-hexane solution of n-butyllthium (15% by weight, 24.6 g, 57.5 mmol) was added dropwise at 10° C. Next, at 10° C., trimethoxyborane (5.7 g, 55.0 mmol) was added dropwise. After 30 minutes from adding dropwise, cooling bath was removed off, and the reaction mixture was stirred at room temperature overnight. However, 6-chloro-3-pyridylboronic acid could not be obtained.

Provenance & Evidence