Cyanogen Bromide → HCID 68154608, compound

Participants

Reaction Steps

The procedure used to prepare 4 cc was repeated using 1 g (3.42 mmol) of 4y and 720 mg (6.84 mmol, 2 equiv) of cyanogen bromide to afford a product that was purified by chromatography (multiple times and each time using two developments) using 1:5 EtOAc-hexane to afford 390 mg (41%) of 4ee as a 9:1 E:Z-mixture of isomers that was a yellow oil. 1H NMR (DMSO-d6): δ 7.49 (d, 2H, J=8.4 Hz), 7.35 (d, 2H, J=8.4 Hz), 7.24 (t, 1H, J=8.0 Hz), 6.99 (d, 1H, J=16.4 Hz), 6.82 (d, 1H, J=16.4 Hz), 6.55 (d, 2H, J=8.4 Hz), 6.01 (q, 1H, J=5.2 Hz), 2.70 (d, 3H, J=J5.2 Hz). 13C NMR (DMSO-d6): δ 150.45, 137.40, 134.69, 133.36, 128.86 (two C), 128.28, 127.97 (two C), 123.47, 116.09 (two C), 111.57 (two C), 29.50. HRMS (EI) Calcd for C15H13Cl2N, 277.0425. Found: 277.0425.

Provenance & Evidence