Chlorotrimethylsilane → (4-Methoxy-dibenzofuran-1-yl)-acetonitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-methoxy-dibenzofuran-1-carbaldehyde (13.5 g, 0.059 mol) in acetonitrile (200 ml) was added LiBr (9.8 g, 0.13 mol) and TMS chloride (11.5 ml, 0.089 mol) at room temperature under stirring. The reaction mass was cooled to 0° C., and at 0° C., 1,1,3,3-tetramethyl disiloxane (17 ml, 0.096 mol) was added drop wise. The reaction mass was allowed slowly to come to room temperature and was stirred for 4 hrs at room temperature. Once TLC confirmed the absence of starting material, the reaction mass was diluted with DCM (300 ml), and filtered through Hyflow. The filtrate was concentrated under vacuum and again dissolved in DCM and filtered. To the brown colored compound DMF (150 ml) was added and the reaction mass was stirred for 10 min, until it dissolved. To the solution NaCN (6.44 g, 0.131 mol) was added and the reaction mass was allowed to stir for 4 hrs at room temperature. The reaction mass was quenched with water and extracted with ethyl acetate. The organic layer was washed with brine, dried with sodium sulfate and concentrated under vacuum to get (4-methoxy-dibenzofuran-1-yl)-acetonitrile, Yield 12 g (85%) 1H-NMR (300 MHz, CDCl3) 7.9 (d, J=7.2, 1H); 7.67 (d, J=8.2, 1H); 7.55 (ddd, J=1.2, 7.3, 8.5, 1H); 7.43 (ddd, J=1, 7.8, 8.5, 1H), 7.29 (d, J=8.2, 1H), 6.98 (d, J=8.2, 1H); 4.15 (s, 2H), 4.0 (s, 3H)

Provenance & Evidence