[F:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:12])[CH:8]=2)[CH:3]=1.C1C(=O)N([Br:20])C(=O)C1.BrBr.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:20][CH2:12][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([F:1])[CH:3]=2)[CH:8]=1To a solution of 2-fluoro-6-methylnaphthalene (0.750 g, 4.68 mmol) in carbon tetrachloride (20 mL) was added NBS (0.917 g, 5.15 mmol) and bromine (0.265 mL, 5.15 mmol) followed by AIBN (0.077 g, 0.47 mmol). The reaction mixture was heated to 70° C. and allowed to stir for 4 hours. It was then cooled to room temperature, partitioned between water and EtOAc, and the aqueous layer was extracted three times with EtOAc. The combined organic layers were dried over sodium sulfate, filtered, concentrated in vacuo and subjected to silica gel chromatography eluting with 5-50% EtOAc in hexanes to yield 2-(bromomethyl)-6-fluoronaphthalene.
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