1,2-Diiodoethane → HCID 58065000, compound

Participants

Reaction Conditions

Reaction Steps

t-Buthyllithium (2.7 mL of a 1.7 M solution in pentane, 4.61 mmol) was added to a solution of 1-(N-tert-Butoxycarbonylamino)-6,7-dimethoxynaphthalene (0.50 g, 1.65 mmol) in dry diethyl ether (5.0 mL) and dry DME (2.5 mL) at −40° C. under nitrogen. The resulting mixture was stirred at −20° C. for 5 h and then cooled to −78° C. A solution of 1,2-diiodoethane (1.30 g, 4.61 mmol) in dry DME was added and the resulting solution was allowed to warm to ambient temperature over several hours. Aq. NH4Cl was added, and the mixture was extracted twice with DCM. The combined organic extracts were washed with water, dried, filtered and evaporated to leave a dark glass. The compound was purified by column chromatography to give the pure product 1-(N-tert-Butoxycarbonylamino)-6,7-dimethoxy-4-iodonaphthalene. 1H NMR (200 MHz) (DMSO-d6) δ 1.51 (s, 9H), 3.82 (s, 3H), 3.97 (s, 3H), 7.42 (t, J=8.5 Hz, 1H), 7.48 (s, 1H), 7.57 (d, J=8.5 Hz, 1H), 7.79 (d, J=8.5 Hz, 1H), 9.28 (s, 1H).

Provenance & Evidence