C([O:4][C:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=1)(=O)C.Br[C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([O:23][CH3:24])[CH:17]=1.C[O-].C([Sn+](CCCC)CCCC)CCC>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[Cl:22][C:19]1[CH:20]=[CH:21][C:16]([CH:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH2:13][CH2:14][C:5]2=[O:4])=[CH:17][C:18]=1[O:23][CH3:24]Charge an oven dried, argon flushed 3-L 3-necked round bottomed flask equipped with a mechanical stirrer and reflux condenser with 2-acetoxy-3,4-dihydronaphthalene (100.69 grams, 0.5349 moles), 4-bromo-2-methoxy-1-chlorobenzene (116.81 grams, 0.5274 moles), palladium acetate (1.19 grams, 0.0053 moles), tri (ο-tolyl)phosphine (3.24 grams, 0.0107 moles), tri-n-butyltin methoxide (172.83 grams, 0.5383 moles) and 1 L toluene. Place in an oil bath pre-heated to 100°-105° C. for 20 hours. Distill off about 750 mL toluene, cool to RT, add 500 mL 5% HCl and 250 mL ethyl acetate, stir for a few minutes, filter through a pad of celite and wash the celite pad with 5×250 mL ethyl acetate. Separate the layers, extract the aqueous layer with 1×250 mL ethyl acetate, wash the combined organic layers with saturated sodium bicarbonate solution followed by saturated salt solution, dry over magnesium sulfate and concentrate on a Buchi rotavapor. Kugelrohr treat the resulting oil (heated to about 130° C., 1 Torr) to remove the more volatile by-products to yield product. An analytical sample can be prepared by flash chromatography (5-30% ethyl acetate/hexanes) followed by recrystallization (ethyl acetate/hexanes).
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