[Br:1][C:2]1[C:11]2[C:6](=[C:7]([OH:12])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[C:13]([O-])([O-])=O.[K+].[K+].S(OC)(OC)(=O)=O.O>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CC#N>[Br:1][C:2]1[C:11]2[C:6](=[C:7]([O:12][CH3:13])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1A suspension of 1-bromo-5-hydroxy-naphthalene (1.56 g, 7.0 mmol, prepared according to patent WO0146181), K2CO3 (1.45 g, 10.5 mmol), tetrabutylammonium chloride (15 mg, 0.05 mmol) and dimethyl sulfate (1.32 ml, 10.5 mmol) in MeCN was refluxed for 1 hour. After the addition of water, the aqueous phase was extracted three times with CH2Cl2. The combined organic layers were washed with water, dried over MgSO4, filtered and the solvent was removed under reduced to provide 1-bromo-5-methoxy-naphthalene (1.05 g, 64%) as a white solid, MS: m/e=236 (M+).
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