Benzene, 1-chloro-4-fluoro- → (5-Chloro-2-fluoro-phenyl)boronic acid

Participants

Reaction Steps

To 30.0 g (23 mmol) of 1-chloro-4-fluorobenzene in THF at −78° C. was added 14.4 mL (23 mmol) of a n-butyllithium solution (1.6M in hexanes). After stirring for 2.5 h at that temperature, 10.6 mL (46 mmol) of triisopropyl borate was added dropwise, and the reaction was allowed to slowly warm to room temperature and stir overnight. The reaction was carefully quenched with 1M HCl and then extracted three times with Et2O. The combined organic phase was washed with water, dried over MgSO4, and concentrated to provide 20-1 as a white powder. Data for 20-1: 1HNMR (500 MHz, CDCl3) δ 7.8 (m, 1H), 7.4 (m, 1H), 7.0 (m, 1H), 5.2 (m, 2H) ppm.

Provenance & Evidence