[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][CH2:10][CH2:9][C:8]([CH2:12]O)=[CH:7][C:6]=2[CH:14]=1.CCN(C(C)C)C(C)C.CS([Cl:28])(=O)=O.C(OCC)C>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][CH2:10][CH2:9][C:8]([CH2:12][Cl:28])=[CH:7][C:6]=2[CH:14]=1
To a solution of (2-bromo-6,7-dihydro-5H-benzo[7]annulen-8-yl)methanol from step A5 (150 mg, 0.593 mmol) in dichloromethane (2 mL) was added DIEA (0.310 mL, 1.78 mmol) followed by methanesulfonyl chloride (0.053 mL, 0.681 mmol) at 0° C. The mixture was gradually warmed up to rt and stirred for 18 h. Diethyl ether (50 mL) was added, the mixture was washed with water, the organic layer was partioned and concentrated. The residue was purified using silica gel column chromatography (hexanes-10% EtOAc) to give 2-bromo-8-(chloromethyl)-6,7-dihydro-5H-benzo[7]annulene (135 mg, 0.497 mmol, 84% yield). 1H NMR (500 MHz, chloroform-d) δ 7.31-7.29 (m, 1H), 7.26 (dd, J=8.2, 1.8 Hz, 1H), 7.00 (d, J=7.9 Hz, 1H), 6.51 (s, 1H), 4.21 (s, 2H), 2.80-2.74 (m, 2H), 2.48 (t, J=6.7 Hz, 2H), 2.10-2.02 (m, 2H).
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