Ethyl Acetate → N-(7-Bromo-3,4-dihydronaphthalen-1(2H)-ylidene)-2-methylpropane-2-sulfinamide

Participants

Reaction Steps

7-Bromo-3,4-dihydronaphthalen-1(2H)-one (5 g, 22.21 mmol), 2-methylpropane-2-sulfinamide (4.04 g, 33.32 mmol) and titanium ethoxide (9.15 mL, 44.43 mmol) were dissolved in 2-Me THF (50 mL) and heated to reflux for 22 h. The reaction was left to cool down to r.t. EtOAc (20 mL), NaHCO3 (sat, 5 mL) and water was added under stirring. The mixture was left to stand without stirring for 1 h. The organic phase was collected by filtration, dried over MgSO4 and concentrated in vacuo to give the title compound (7.29 g) that was used without purification in the next step: 1H NMR (500 MHz, CDCl3) δ ppm 1.34 (s, 9H), 2.00-2.10 (m, 2H), 2.77-2.86 (m, 2H), 3.01-3.12 (m, 1H), 3.28 (ddd, 1H), 7.09 (d, 1H), 7.50 (dd, 1H), 8.25 (d, 1H), MS (ES+) m/z 328[M+H]

Provenance & Evidence