Water → HCID 54369541, compound

Participants

Reaction Steps

27 ml of a 1.5 M solution of t-butyllithium in pentane are added over the course of 1.5 hours at -78° C. to a solution of 4.42 g (0.02 mol) of 1-bromo-2-methylnaphthalene in 40 ml of THF. The reaction mixture is stirred for 1 hour. 1.1 ml of phenyldifluoroborane (1.26 g, 0.01 mol) are added. The mixture is then allowed to warm to room temperature and is stirred for 2 hours more. The mixture is poured into 300 ml of water and the resulting suspension is filtered. The product is purified by chromatography (SiO2, hexane), to give 1.43 g (i.e. 39% of theory) of the borane as a white solid with a melting point of 208-209° C. The 1H-NMR shifts δ measured in CDCl3 are: 7.72 ppm (d,4,J=8.3 Hz), 7.53 ppm (d,2,J=8.6 Hz), 7.40-7.35 ppm (m,3), 7.25-7.15 ppm (m,6), 7.03 ppm (t,2,J=7 Hz) and 2.16 ppm (s,6).

Provenance & Evidence