Water → 6-Bromo-1-chloronaphthalen-2-ol

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Reaction Steps

A mixture of 6-bromo-2-naphthol (20.0 g, 89.7 mmol) and sulfuryl chloride (14.4 mL, 180 mmol) in chloroform (220 mL) was refluxed for 30 minutes. It was then stirred, while cooling to ambient temperature, for one hour. Water (100 mL) was added to the reaction mixture. The organic phase was washed with brine, dried with anhydrous magnesium sulfate, filtered and solvent evaporated. The residue was recrystallized in hot hexane. It was rinsed with cold acetone and dried in vacuo at 60° C. for 30 minutes to yield 6-bromo-1-chloro-naphthalen-2-ol as a tan solid (11.2 g, 48.3%): MP: 100–1° C.; Mass spectrum (−ES, [M−H]−) m/z 255, 257, 259. 1HNMR (500 MHz, DMSO-d6): δ 10.63 (s, 1H), 8.15 (d, 1H, J=1.8 Hz), 7.95 (d, 1H, J=9.0 Hz), 7.77 (d, 1H, J=9 Hz), 7.68 (dd, 1H, J=9.0, 1.8 Hz), and 7.32 ppm (d, 1H, J=8.85 Hz). Elemental Analysis for C10H6BrClO: Calculated: C, 46.64; H, 2.35; N, 0.00. Found: C, 46.69; H, 2.35; N, 0.00.

Provenance & Evidence