Diiodomethane → HCID 86631946, compound

Participants

Reaction Steps

1-tert-Butyl 4-methyl 3-amino-2,5-dimethylterephthalate (0.444 g, 1.59 mmol) was dissolved in THF (10 mL), and the mixture was sparged with nitrogen for 10 minutes. Copper (I) iodide (302 mg, 1.59 mmol) and diiodomethane (0.64 mL, 7.93 mmol) were added followed by isoamyl nitrite (0.63 mL, 4.74 mmol), and the mixture was stirred at reflux for 20 h. The mixture was cooled to ambient temperature and then was partitioned between ethyl acetate and 1N hydrochloric acid. The aqueous portion was extracted with ethyl acetate (2×). The combined organic portion was washed with brine, dried over sodium sulfate, then filtered and concentrated to provide an oil which was purified by column chromatography (silica gel, 2-10% ethyl acetate in hexanes). The clean fractions were combined and concentrated, and the residue was partitioned between ethyl acetate and 1: I saturated sodium bicarbonate solution: 1 M sodium thiosulfate. The aqueous portion was extracted with ethyl acetate. The combined organic portion was washed with brine, dried over sodium sulfate, then filtered and concentrated to afford 1-tert-butyl 4-methyl 3-iodo-2,5-dimethylterephthalate (300 mg, 0.769 mmol, 48% yield) as a yellow oil. 1H NMR (400 MHz, CDCl3): δ 7.42 (s, 1H), 3.96 (s, 3H), 2.60 (s, 3H), 2.31 (s, 3H), 1.59 (s, 9H); GCMS for C15H19IO4: 359 ([M-OCH3]+).

Provenance & Evidence