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• Preparation

  Add a concentrated solution of 8-bromo-naphthyl-1-amine (4.48 g, 20 mmol) to a solution of HCl (30 mL) and H₂O (25 mL) at 0°C. Add a solution of NaNO₂ (3.45 g, 50 mmol) in H₂O (10 mL). Dissolve freshly prepared CuCl (13.86 g, 140 mmol) in a concentrated solution. Add HCl (15 mL) to the reaction mixture. Bring the reaction mixture to room temperature and stir at 65°C for 30 minutes. Add ethyl acetate (250 mL), separate the organic layer, wash with H₂O (3 × 100 mL) and brine, dry with Na₂SO₄, and evaporate under vacuum. Purify by chromatography on silica, eluting with CHCl₃, then to CHCl₃:MeOH (98:2), to give the oily second intermediate compound 1-Bromo-8-chloronaphthalene (2.95 g, 72%).;

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