Boron tribromide → 8-Fluoronaphthalen-2-ol

Participants

Reaction Steps

The title compound was prepared by reacting 1-fluoro-7-methoxynaphthalene (7.99 g, 45.34 mmol) with boron tribromide (68 mL of 1N solution, 68 mmol) according to method D to yield 3.99 g (54%) of a red solid. An analytical sample was prepared by preparative reverse phase HPLC to yield a white solid: mp 89–92° C.; 1H NMR (DMSO-d6): δ 7.16 (1H, dd, J=2.42 Hz, J=8.90 Hz), 7.21–7.25 (3H, m), 7.62–7.65 (1H, m), 7.85 (1H, dd, J=1.72 Hz, J=8.87 Hz), 10.08 (1H, s); MS (ESI) m/z 161 (M−H)−.

Provenance & Evidence