[Br:1][C:2]1[C:3]([OH:12])=[CH:4][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1.[C:13]([O-])([O-])=O.[K+].[K+].IC>CN(C=O)C>[CH3:13][O:12][C:3]1[C:2]([Br:1])=[CH:11][C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=1A 21 mL oven dried scintillation vial with a Teflon lined cap was charged with 3-bromo-5,6,7,8-tetrahydronaphthalen-2-ol (568 mg, 2.50 mmol), powdered K2CO3 (691 mg, 5.00 mmol), dry DMF (7 mL) and iodomethane (0.622 mL, 10.00 mmol). The flask was purged with N2 sealed and heated on the orbital shaker to 50° C. for 4 hours. After cooling the reaction to ambient temperature, it was concentrated under high vacuum to remove DMF, and then partitioned between brine:water (1:1) and ethyl acetate (2×). The organics were combined, dried with Na2SO4, filtered and concentrated to a crude paste. The crude was purified by Biotage MPLC (90 g column, 2.5% ethyl acetate in heptane) to give 571 mg (94%) of 3-bromo-5,6,7,8-tetrahydronaphthalen-2-yl methyl ether as a white solid. Rf 0.57 (10% ethyl acetate in heptane) 1H NMR shows ˜6% contamination with the 1-bromo regio-iosmer. 1H NMR (400 MHz, CDCl3) δ 7.23 (s, 1 H), 6.59 (s, 1 H), 3.85 (s, 3 H), 2.69 (m, 4 H), 1.76 (m, 4 H); 13C NMR (100 MHz, CDCl3) δ 153.4, 137.4, 133.4, 130.8, 112.4, 108.3, 56.2, 29.5, 28.3, 23.1, 22.9.
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