Dimethylformamide → 6-Methylbenzofuran-2-carbonitrile

Participants

Reaction Conditions

Reaction Steps

To a 500 mL 3-neck flask was added 2-(2,2-dibromovinyl)-5-methylphenol (17.7 g, 60.6 mmol), CuI (1.16 g, 6.06 mmol), Na2CO3 (12.85 g, 121 mmol) and DMF (120 mL). The reaction was heated to 80° C. for 6 hr. After 6 hr the r×n was cooled to RT and anhydrous K4Fe(CN)6 (4.47 g, 12.12 mmol), Pd(OAc)2 (2.04 g, 3.03 mmol) and PPh3 (0.32 g, 1.21 mmol) were added to the reaction and the reaction was flushed with nitrogen for 10 min. The reaction was then heated to 120° C. for 18 hr. After 18 hr the r×n was cooled to RT and diluted with EtOAc. The reaction mixture was filtered through a silica plug to remove solids and flushed with EtOAc. The collected filtrates were diluted with water and brine and extracted with EtOAc×2. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude mixture was purified via silica gel FCC, 100% Heptane-20% EtOAc/80% Heptane to give a yellow solid, 6-methylbenzofuran-2-carbonitrile (5.1 g). 1H NMR (400 MHz, DMSO-d6) δ 2.47 (s, 3H), 7.27 (ddd, J=8.2, 1.4, 0.7 Hz, 1H), 7.57 (s, 1H), 7.71 (d, J=8.1 Hz, 1H), 8.05 (d, J=1.0 Hz, 1H).

Provenance & Evidence