Methanol → HCID 72335435, compound

Participants

Reaction Steps

A mixture of 2-(3-bromo-4-fluorobenzoyl)benzonitrile (Scheme #11, E) and tetraethyl orthotitanate (1 M solution in tetrahydrofuran, 18.3 mL, 18.3 mmol) was stirred for 5 minutes, then 2-methyl-2-propanesulfinamide (1.11 g, 9.13 mmol) was added and the resulting mixture was heated to reflux over night. When the reaction had cooled to room temperature methanol, aqueous saturated sodium bicarbonate and ethyl acetate was added. After filtering the reaction mixture through a pad of sodium sulfate, the filtrate was concentrated. Purification of the residue by column chromatography using chloroform as the eluent gave the title compound (1.22 g, 30% over 2 steps). 1H NMR (CDCl3) δ 7.90-7.69 (m, 3 H), 7.68-7.39 (m, 3 H), 7.18 (t, J=8.21 Hz, 1 H), 1.38 (br s, 9 H); MS (AP) m/z 407, 409 [M+1]+.

Provenance & Evidence