Br[C:2]1[C:15]2[C:6](=[C:7]3[C:12](=[CH:13][CH:14]=2)[C:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:10][CH:9]=[N:8]3)[N:5]=[CH:4][CH:3]=1.[Li]CCCC.[B:27](OC)([O:30]C)[O:28]C.Cl>C1COCC1.CCCCCC>[C:16]1([C:11]2[C:12]3[C:7]([N:8]=[CH:9][CH:10]=2)=[C:6]2[C:15]([C:2]([B:27]([OH:30])[OH:28])=[CH:3][CH:4]=[N:5]2)=[CH:14][CH:13]=3)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=14-Bromo-7-phenyl-1,10-phenanthroline (1.42 g) is dissolved in THF solvent (15 mL). The mixture is cooled to −39° C. and added over a period of 20 minutes to an n-hexane solution of n-BuLi (1.5 M; 3.12 mL) which has been cooled to −78° C. The reaction mixture is stirred for 30 minutes, followed by the addition of trimethyl borate (0.49 mL) in THF at −39° C. is added over a period of 20 minutes. The reaction mixture is maintained at −78° C. for one hour, then allowed to warn to room temperature over a day. The reaction mixture is acidified with cold 2N HCl extracted with ether. The organic layer is extracted with 1 N NaOH and filtered. To the filtrate is added 2 N HCl at 0° C. to yield a precipitate, which is filtered, washed, dried and re-crystallized from ethanol to give the desired product.
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