2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-benzyloxy-4-bromomethyl-1-nitrobenzene (2.99 g, 9.27 mmol) and Pd(PPh3)4 (536 mg, 0.464 mmol) in DME (10 mL) is heated to 60° C. for 2 min. in a microwave. 2-methyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzonitrile (5.96 g of crude, ˜13.9 mmol) in DME (10 mL) and EtOH (2 mL) is added along with Na2CO3 (2 M, 3.3 mL). The reaction mixture is heated to 110° C. for 30 min. by microwave. Then the reaction is heated to 120° C. for an additional 15 min. by microwave. The reaction mixture is diluted with DCM (150 mL) and extracted with water (50 mL). The aqueous layer is extracted with DCM (30 mL) and the combined organics is dried over Na2SO4. Evaporation yields a brown oil, and it is then purified by flash column to yield a tan solid as the title compound: MS (M−H)−=357.2. The reaction mixture is heated to 110° C. for 30 min. by microwave Then the reaction is heated to 120° C. for an additional 15 min. by microwave extracted with water (50 mL) The aqueous layer is extracted with DCM (30 mL) the combined organics is dried over Na2SO4 Evaporation yields a brown oil, and it is then purified by flash column