[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][CH:15]=[C:16]2N)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N([O-])=O.[Na+].[I-:24].[K+]>Cl.O.O1CCCC1>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][CH:15]=[C:16]2[I:24])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
A solution of 7-benzyloxy-naphthalen-1-ylamine (6.98 g, 28.02 mmol) in concentrated hydrogen chloride (30 mL), water (30 mL) and tetrahydrofuran (30 mL) is cooled with an ice-salt (sodium chloride) bath. A solution of sodium nitrite (2.32 g, 33.6 mmol) in water (20 mL) is then added in a dropwise manner over a 15-minute period of time and the reaction temperature is kept under 5° C. The mixture is stirred for another 30 minutes before potassium iodide (9.3 g, 56.04 mmol) in water (30 mL) is added. The resulting mixture is stirred for three hours at room temperature before being extracted with ethyl acetate, dried over sodium sulfate, filtered, concentrated and purified by silica gel chromatography (Hexanes/CH2Cl2 =25/1-20/1) to give 7-benzyloxy-1-iodo-naphthalene (6.26 g, 61%); MS m/z (M+Na+) 361.00.
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