Iodoethane → HCID 21829131, compound

Participants

Reaction Steps

Iodoethane (1.93 mL, 38.4 mmol) was added dropwise over 15 min. to a stirred mixture of 4-nitroguaiacol 1 (5.00 g, 29.6 mmol) and K2CO3 (6.21 g, 44.3 mmol) in DMF (30 ml) at 60° C. under nitrogen. After 2 h the reaction was cooled to RT and diluted with water (100 ml) and methyl tert-butyl ether (250 ml). The organic layer was washed with water (25 ml), brine (2×20 ml), dried over Na2SO4, filtered and concentrated under vacuum to afford 2-ethoxy-5-nitroanisole (5.74 g) as a pale yellow solid. mp 88-90° C. 1H NMR (DMSO-d6) δ 7.89 (dd, 1H), 7.73 (d, 1H), 7.16 (d, 1H), 4.17 (q, 2H), 3.88 (s, 3H), 1.37 (t, 3H). 13C NMR (DMSO-d6) δ 153.9, 148.6, 140.5, 117.6, 111.5, 106.4, 64.6, 55.9, 14.4. MS (ESI+) for m/z 198 [M+H]+.

Provenance & Evidence