(3-Bromopropoxy)(tert-butyl)dimethylsilane → HCID 9835846, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofurancarbonitrile (13.4 g, 60 mmol) in THF (450 mL) was added to a solution of LDA (76 mmol) in THF (30 mL) at −78° C. under an atmosphere of nitrogen. After stirring at −78° C. for 30 min, a solution of (3-bromopropoxy)-tert-butyldimethylsilane (16.8 mL, 72 mmol) in THF (30 mL) was added and the resulting mixture was allowed to warm to room temperature and stirred for 2 h. Then the mixture was poured into ice/H2O (400 mL), and extracted with Et2O (3×500 mL). The organic extracts were washed with H2O (500 mL) and brine (500 mL), dried and evaporated. The residue was dissolved in methanol (400 mL) and was added 1M HCl (200 mL). The resulting solution was stirred at room temperature for 1 h and evaporated. Silica gel chromatography (heptane, EtOAc 5:1) of the residue gave the title product as an oil (14.4 g, 81%). 1H NMR (DMSO-d6) δ1.25 (2H, m); 2.18 (2H, t, J=8.8 Hz); 3.31 (2H, q, J=6.2 Hz); 4.34 (1H, t, J=6.2 Hz); 5.12 (1H, d, J=13.2 Hz); 5.17 (1H, d, J=13.2 Hz); 7.15 (2H, t, J=8.8 Hz); 7.58 (2H, dd, J=6.0 and 8.8 Hz); 7.72 (1H, s); 7.78 (2H, br d, J=6.0 Hz.). 13C NMR (DMSO-d—6) δ27.4; 37.3; 59.8; 71.0; 90.7; 110.5; 114.8; 115.2; 118.8; 123.2; 125.6; 126.9; 127.1; 132.0; 139.9; 140.6; 149.5; 160.9; 162.0.

Provenance & Evidence