4-Iodophenol → HCID 17607451, compound

Participants

Reaction Steps

Alkylation of 4-iodophenol with 2-(bromomethyl)oxirane (76) as in Example 2A for 52 h, followed by chromatography of the product on silica gel, eluting with 0-10% CH2Cl2/petroleum ether (foreruns) and then with 20-25% CH2Cl2/petroleum ether, gave 2-[(4-iodophenoxy)methyl]oxirane (79) (reported by Apparu et al., 2000 using glycidyl tosylate) (89%) as a white solid: mp (CH2Cl2/petroleum ether) 67-68° C.; 1H NMR (CDCl3) δ 7.56 (dt, J=9.0, 2.7 Hz, 2H), 6.70 (dt, J=9.0, 2.7 Hz, 2H), 4.20 (dd, J=11.1, 3.1 Hz, 1H), 3.92 (dd, J=11.1, 5.7 Hz, 1H), 3.33 (m, 1H), 2.90 (dd, J=4.8, 4.3 Hz, 1H), 2.74 (dd, J=4.9, 2.6 Hz, 1H).

Provenance & Evidence