C[Si](C)(C)[O:3][C:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.Br[C:35]1[CH:40]=[CH:39][C:38]([Cl:41])=[C:37]([O:42][CH3:43])[CH:36]=1.CN(C)C=O>C(OC)(C)(C)C.O>[Cl:41][C:38]1[CH:39]=[CH:40][C:35]([CH:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:12][CH2:13][C:4]2=[O:3])=[CH:36][C:37]=1[O:42][CH3:43]
Charge an oven dried, argon flushed 25-mL 2-necked round bottomed flask equipped with a stirring bar and reflux condenser with 2-trimethylsilyloxy-3,4-dihydronaphthalene (0.4247 grams, 1.9449 mmoles) and tetra-n-butylammonium fluoride (2.3 mL, 2.30 mmoles, 1 M in tetrahydrofuran), stir for a few minutes and then add 4-bromo-2-methoxy-1-chlorobenzene (0.4336 grams, 1.9577 mmoles) dichlorobis(tri-ο-tolyl-phosphine)palladium (0.0154 grams, 0.0196 mmoles) and 5 mL dimethylformamide. Heat the reaction mixture for 18 hours (oil bath temperature about 90° C.), cool to RT and add 5 mL water and 10 mL t-butylmethyl ether. Separate the layers, extract the aqueous layers with 3×5 mL t-butylmethyl ether, wash the combined organic layers with water and saturated salt solution, dry over magnesium sulfate and concentrate using a Buchi rotavapor to yield the final product.
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