Allyl bromide → HCID 58361498, compound

Participants

Reaction Steps

A mixture of compound 16 (448 mg, 1.14 mmol), In powder (150 mg, 1.31 mmol) and allyl bromide (160 μL, 1.87 mmol) were stirred in a mixture of 10 mL THF and 10 mL aq. NH4Cl for 3 hours. THF was removed in vacuo, and residue was extracted with EtOAc and then dried over anhydrous Na2SO4. Solvent was removed in vacuo, and the residue was purified by SiO2 column chromatography (hexanes/EtOAc=2/1) to yield 17 as a colorless oil (478 mg, 1.10 mmol, 96% yield). 1H NMR (500 MHz, CDCl3) δ 8.13 (d, 1H, J=8.0 Hz), 7.96−7.93 (m, 2H), 7.76 (d, 1H, J=9.0 Hz), 7.68 (t, 1H, J=8.5 Hz), 7.54−7.50 (m, 3H), 7.42 (d, 1H, J=8.5 Hz), 5.89−5.80 (m, 1H), 5.11−5.03 (m, 2H), 4.97 (s, 2H), 2.73−2.69 (m, 1H), 2.54−2.48 (m, 1H). 13C NMR (500 MHz, CDCl3) δ 163.40, 148.17, 144.08, 137.34, 135.61, 134.86, 133.88, 129.40, 128.67, 128.01, 126.84, 122.47, 119.53, 118.22, 118.12, 72.24, 42.34. MS-ESI (m/z): [M+H]+ calculated for C19H17BrNO4S, 434.01 (79Br) and 436.00 (81Br); found 434.11 (79Br) and 436.10 (81Br).

Provenance & Evidence