C([Li])CCC.[CH3:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].BrC1C=CC=CC=1.[C:19]1([CH3:38])[CH:24]=[C:23]([CH3:25])[CH:22]=[C:21]([CH3:26])[C:20]=1[B:27]([C:29]1[C:34]([CH3:35])=[CH:33][C:32]([CH3:36])=[CH:31][C:30]=1[CH3:37])F>O1CCCC1.O>[C:19]1([CH3:38])[CH:24]=[C:23]([CH3:25])[CH:22]=[C:21]([CH3:26])[C:20]=1[B:27]([C:29]1[C:34]([CH3:35])=[CH:33][C:32]([CH3:36])=[CH:31][C:30]=1[CH3:37])[C:8]1[CH:7]=[CH:6][CH:11]=[CH:10][CH:9]=11.1 equivalents of 1.6 M butyllithium in hexane (37.5 ml, 0.066 mol) are added over the course of 15 minutes at -78° C. to a solution of 9.42 g (0.06 mol) of bromobenzene in 80 ml of tetrahydrofuran (THF). The reaction mixture is stirred at this temperature for 3 h. Then 16.1 g (0.06 mol) of solid dimesitylfluoroborane are added, and the mixture is allowed to warm to room temperature and stirred for a further hour. The mixture is poured into 500 ml of water and the resulting suspension is filtered. The product is purified by trituration with boiling methanol, to give 16.9 g (86% of theory) of the product as a white solid with a melting range of 185-187° C. The shifts δ in the 1H NMR, measured in CDCl3 are 7.50 ppm (d,2,J=7 Hz), 7.46 ppm (t,1,J=10 Hz), 7.50 ppm (br t, 2, J=7 Hz), 6.82 ppm (s, 4), 2.30 ppm (s,6) and 2.00 ppm (s,12).
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