1,8-Diaminonaphthalene → 2-(3-Chloro-4-fluorophenyl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine

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Reaction Steps

A solution of 3-chloro-4-fluorobenzene boronic acid (4 g, 22.8 mmol) and naphthalene-1,8-diamine (3.62 g, 22.9 mol) in anhydrous toluene (80 mL) was heated to reflux for 4 hours. The reaction mixture was cooled to room temperature, then concentrated in vacuo. The residue was trituated with hexane to afford the title compound as a grey solid in 88% yield, 6 g.

Provenance & Evidence