Bromine → HCID 67301096, compound

Participants

Reaction Conditions

Reaction Steps

2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)oxazole (201 mg, 0.554 mmol) was dissolved in anhydrous THF (5 mL), cooled to −78° C. and t-BuLi (1.7 M in pentane, 1.3 equiv) was added dropwise under Ar. The reaction mixture was stirred for 2 h at −40° C., cooled to −78° C. and bromine (3 equiv) was added dropwise. The reaction mixture was warmed to room temperature, diluted with EtOAc, washed with saturated Na2S2O3, washed with saturated aqueous NaCl and dried over Na2SO4. Evaporation in vacuo yielded the crude aryl bromide, which was purified by flash chromatography (0-1.5% EtOAc/hexanes) to afford the title compound as a clear oil (218 mg, 90%): 1H NMR (CDCl3, 600 MHz) 7.28-7.26 (m, 2H), 7.17-7.16 (m, 3H), 6.92 (s, 1H), 4.74 (t, 1H, J=7.2 Hz), 2.59 (t, 2H, J=7.8 Hz), 1.90-1.79 (m, 2H), 1.60-1.59 (m, 2H), 1.53-1.34 (m, 6H), 0.88 (s, 9H), 0.07 (s, 3H), −0.02 (s, 3H); 13C NMR (CDCl3, 150 MHz) δ 167.8, 143.6, 129.3, 129.1, 127.7, 126.5, 122.1, 69.5, 37.0, 36.8, 32.3, 30.0, 26.6, 26.6, 25.9, 19.1, −4.1, −4.3.

Provenance & Evidence