Diethyl Ether → HCID 2737238, compound

Participants

Reaction Steps

n-Butyl lithium (31.3 ml of a 1.6M solution in hexane) was added to a stirred solution of 3-bromopyridine (4.8 ml) and trimethyl borate (6.2 ml) in dry THF (100 ml) at a rate such that the temperature did not exceed -65° C. The mixture was allowed to warm to ambient temperature over 16 hours and was filtered. The solid was washed with ether, combined with more solid obtained from the filtrate and rewashed with ether to give dimethoxy-(3-pyridyl)borane (3.5 g) as a solid, 1H NMR (CD3OD): 3.4 (s, 6 H), 7.2 (m, 1 H), 7.9 (m, 1 H), 8.2 (dd, 1 H), 8.6 (s, 1 H); mass spectrum (+ve CI): 152 (M+H)+.

Provenance & Evidence