p-Toluenesulfonic acid → HCID 60167285, compound

Participants

Reaction Conditions

Reaction Steps

Carbamate 10 (1.20 g, 2.80 mmol) was dissolved in freshly distilled THF (0.17 M) under Ar and in the absence of light, and TsOH□H2O (53 mg, 0.28 mmol) and N-iodosuccinamide (753 mg, 3.30 mmol) were added. The reaction mixture was allowed to stir at 25° C. for 2 h. After 2 h, the reaction was quenched with the addition saturated aqueous NaHCO3 and diluted with ethyl acetate. The organic layer was washed with saturated aqueous NaCl, dried over Na2SO4, and concentrated under reduced pressure. Flash chromatography (SiO2, 5×16 cm, 5% EtOAc/hexanes elution) provided 11 (1.47 g, 94%) as an orange solid. 1H NMR (CDCl3, 500 MHz) δ 8.16 (s, 1H), 8.09 (d, J=8.0 Hz, 1H), 7.70 (d, J=7.5 Hz, 1H), 7.62 (d, J=7.0 Hz, 2H), 7.39 (t, J=7.2 Hz, 2H), 7.34 (d, J=7.0 Hz, 1H), 7.32 (s, 1H), 7.25-7.22 (m, 2H), 5.28 (s, 2H), 1.58 (s, 9H). 13C NMR (CDCl3, 125 MHz) δ 155.8, 152.4, 139.0, 136.7, 135.9, 132.2, 131.9, 130.0, 128.5, 128.3, 128.0, 127.9, 121.4, 120.2, 120.1, 117.0, 101.9, 81.3, 71.3, 28.3. IR (film) νmax 3378, 2978, 1730, 1225, 1145 cm−1. ESI-TOF HRMS m/z 553.9820 (M+H+, C22H21BrINO3 requires 553.9822).

Provenance & Evidence