[CH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[OH:11].C1C(=O)N([Br:19])C(=O)C1>CN(C=O)C>[Br:19][C:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[OH:11]To a solution of 5,6,7,8-tetrahydro-2-naphthol (2.50 g, 16.9 mmol) in DMF (5 mL), is added dropswise NBS (3.0 g, 16.9 mmol). The solution is stirred at room temperature for 18 h. The mixture is washed with water, extracted with CH2Cl2, dried over MgSO4 and concentrated. The crude material is purified via Biotage, eluting with 5-40% EtOAc/hexanes to afford 1-bromo-5,6,7,8-tetrahydronaphthalen-2-ol.
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