4-Iodophenol → HCID 66956448, compound

Participants

Reaction Steps

Reaction of epoxide 140 (see Example 2B) with 4-iodophenol as in Example 2AA at 83° C. for 8 h, followed by chromatography of the product on silica gel, eluting with 0-2% EtOAc/CH2Cl2 (foreruns) and then with 5% EtOAc/CH2Cl2, gave 4-(2-chloro-4-nitro-1H-imidazol-1-yl)-1-(4-iodophenoxy)-2-methyl-2-butanol (143) (81%) as a cream solid: mp (CH2Cl2/pentane) 91-93° C.; 1H NMR (CDCl3) δ 7.80 (s, 1H), 7.59 (dt, J=8.9, 2.6 Hz, 1H), 6.69 (dt, J=8.9, 2.6 Hz, 1H), 4.28 (ddd, J=14.1, 9.6, 6.3 Hz, 1H), 4.23 (ddd, J=14.1, 9.4, 6.5 Hz, 1H), 3.82 (d, J=9.0 Hz, 1H), 3.79 (d, J=9.0 Hz, 1H), 2.22 (ddd, J=13.8, 9.2, 6.5 Hz, 1 H), 2.20 (s, 1H), 2.02 (ddd, J=13.8, 9.6, 6.6 Hz, 1H), 1.39 (s, 3H); HRESIMS calcd for C14H16ClIN3O4 m/z [M+H]+ 453.9840, 451.9869. found 453.9832, 451.9857.

Provenance & Evidence