[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]#[N:10])[CH:4]=1)#[N:2].[Li+].CC([N-]C(C)C)C.[B:19](OC)([O:22]C)[O:20]C.O>C1COCC1.CC(O)=O>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]#[N:10])[C:4]=1[B:19]([OH:22])[OH:20])#[N:2]1,3-Dicyanobenzene (1.00 g) was dissolved in freshly distilled THF (70 mL). This solution was cooled to −96° C. and LDA (4.2 mL of a 2M solution) was added dropwise to the cold solution under N2. The mixture was stirred for 30 min at −96° C. and (MeO)3B (1.3 mL) was added. The resulting mixture was allowed to warm to room temperature and stirred overnight. Water was added and the resulting mixture was stirred for 0.5 h, then acidified with HOAc and extracted with EtOAc. The organic layer was further washed with water and brine, dried (MgSO4), filtered and evaporated. The residue was taken up in CH2Cl2, filtered and evaporated to yield 2,6-dicyanobenzeneboronic acid (0.56 g).
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