Dimethyl Sulfoxide → HCID 57626401, compound

Participants

Reaction Steps

To a stirred solution of the bromide 5 (12.82 g, 55 mmol) dissolved in DMSO (60 mL) was added dry KCN (1.95 g, 30 mmol), and the reaction mixture was stirred at 40° C. for 3.5 hours until the KCN powder had disappeared. The reaction was quenched with saturated aqueous NH4Cl solution (150 mL). After extraction with ethyl acetate, the combined organic layers were washed with 1N NaOH, water, and brine. After drying over Na2SO4, the organic layer was filtered and ethyl acetate was evaporated in vacuo. The residue was then vacuum distilled at 130-135° C. at 1.0 mm Hg to give 5.35 g (54.6%) of product as a colorless oil. Further distillation yielded 5.8 g (45.2%) of recovered bromide 5. 1H NMR (CDCl3) δ 7.01-6.98 (m, 2H), 6.90-6.87 (m, 2H), 4.55-4.52 (m, 1H), 2.68 (d, J=5.5 Hz, 2H), 1.48 (d, J=6.5 Hz, 3H). EI-MS (m/z) 179 (M++1). The reaction is shown as follows.

Provenance & Evidence