Sodium Bicarbonate → HCID 59596236, compound

Participants

Reaction Conditions

Reaction Steps

Titanium(IV) ethoxide (1M in tetrahydrofuran, 7.07 mL, 7.07 mmol) was added to 2-(3-bromobenzoyl)-4-chlorobenzonitrile (Scheme #18 R, 1.03 g, 3.21 mmol) at room temperature under argon atmosphere. 2-Methyl-2-propanesulfinamide (0.428 g, 3.53 mmol) was added 2 minutes later. The reaction mixture was refluxed overnight and then stirred at 50° C. for 24 h. The mixture was cooled to ambient temperature and diluted with methanol (7 mL). Saturated aqueous sodium bicarbonate was added and the mixture was diluted with ethyl acetate. The gelatinous precipitate formed was filtered off through a pad of magnesium sulfate (top) and diatomaceous earth (bottom). The filtrate was concentrated and the residue was purified by flash chromatography using ethyl acetate in heptane (0-40%) affording 0.956 g (70% yield) of the title compound. 1H NMR (DMSO-d6) δ 8.01 (d, J=6.53 Hz, 1 H), 7.95-7.75 (m, 3 H), 7.71 (s, 1 H), 7.52-7.44 (m, 2 H), 1.28 (s, 9 H).

Provenance & Evidence