[Mg].[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9]Cl)=[CH:5][CH:4]=1.[Cl-].Br[C:13]1[CH2:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[CH:17][CH:16]=2>CCOCC.Cl[Ni]1(Cl)[P](C2C=CC=CC=2)(C2C=CC=CC=2)CCC[P]1(C1C=CC=CC=1)C1C=CC=CC=1>[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:13]2[CH2:21][C:20]3[C:15]([CH:14]=2)=[CH:16][CH:17]=[CH:18][CH:19]=3)=[CH:5][CH:4]=1To a suspension of freshly ground magnesium (0.58 g, 23 mmol) in 100 mL of ether was added about 3 mL of a 15 mL ether solution containing 3.0 g (21 mmol) of 4-fluorophenylmethyl chloride. The system was carefully heated and after initiation of the reaction, the remaining chloride solution added over 30 minutes while maintain a gentle reflux. After refluxing for 1.5 hours, the Grignard solution was cooled and cannulated to a mixture of 3.65 g (19 mmol) of 2-bromo-indene, 150 mg (0.20 mmol) of NiCl2(dppp) and 100 mL of ether. The system was gently heated to reflux overnight and then cooled and quenched by adding 150 mL of 1.0 M aqueous hydrochloric acid. The product was isolated and purified (hexanes/silica) as for 2-benzyl-indene. Yield: 3.45 g, 74 percent
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