反应详情

A solution of 4-bromo-3-methoxybenzonitrile (Combi-Blocks, San Diego, Calif., 2.500 g, 11.79 mmol) in 100 mL of diethyl ether was cooled to −78° C. and was treated with n-butyllithium (4.95 ml, 12.38 mmol). After stirring for 10 minutes, 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (3.07 ml, 16.51 mmol) was added, and the cooling bath was removed. After stirring for an additional 2 hours, LC/MS showed mostly product, so the reaction mixture was quenched with saturated NH4Cl solution. After stirring for 20 minutes, the reaction mixture was poured into a separatory funnel charged with EtOAc. The organic layer was separated, dried over MgSO4 and concentrated. Purification of the crude residue by silica gel column chromatography (0 to 100% EtOAc/heptane) gave 3-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (1.62 g, 6.25 mmol, 53.0% yield) with minor impurities. m/z (ESI) 260.1 (M+H)+

1. customthe cooling bath was removed
2. stirringAfter stirring for an additional 2 hours
3. customso the reaction mixture was quenched with saturated NH4Cl solution
4. stirringAfter stirring for 20 minutes
5. additionthe reaction mixture was poured into a separatory funnel
6. additioncharged with EtOAc
7. customThe organic layer was separated
8. dry with materialdried over MgSO4
9. concentrationconcentrated
10. customPurification of the crude residue by silica gel column chromatography (0 to 100% EtOAc/heptane)