Pentane → HCID 58993526, compound

Participants

Reaction Steps

To a solution of (±)-3′-chloro-5′-(1-hydroxyethyl)biphenyl-4-carbonitrile (171 mg, 0.664 mmol) and carbon tetrabromide (264 mg, 0.796 mmol) in tetrahydrofuran (2 mL) at 0° C. was added triphenylphosphine (209 mg, 0.796 mmol). The resulting solution was stirred at room temperature for 45 min. The reaction was diluted with ca. 2 volumes of pentane and filtered to remove the undissolved solids which were discarded. The organics were concentrated and purified by column chromatography (3%→8% ethyl acetate/hexanes) to give 201 mg (94%) as a colorless oil. 1H-NMR (CDCl3, 500 MHz) δ 7.74 (d, J=8.2 Hz, 2H), 7.66 (d, J=8.2 Hz, 2H), 7.50 (s, 1H), 7.47 (s, 2H), 5.18 (q, J=6.7 Hz, 1H), 2.06 (d, J=7.0 Hz, 3H); 13C NMR (126 MHz, CDCl3) δ ppm 146.1, 143.8, 141.5, 135.4, 132.8, 127.9, 127.3, 127.1, 124.2, 118.6, 112.1, 47.4, 26.8.

Provenance & Evidence