2,4,5-Trichlorophenol → HCID 67852021, compound

Participants

Reaction Steps

A solution of acid in Example 20a (195 mg, 0.57 mmol) in 8 mL anhydrous methylene chloride was treated with 2,4,5-trichlorophenol (112 mg, 0.57 mmol) and EDCI (160 mg, 0.85 mmol). The reaction mixture was stirred for 24 hours at ambient temperature under nitrogen atmosphere. The mixture was washed with 10% citric acid and brine. The organic layer was dried over anhydrous sodium sulfate and concentrated to yield a residue that was purified by flash chromatography on silica gel. Elution with EtOAc/hexane (1/5~1/1, v/v, with 1% HOAc) afforded the title compound (158 mg, 54% yield) as an oil: 1H NMR (CDCl3, 60 MHz) δ1.45 (s, 9H), 2.58 (q, 2H), 3.28 (q, 2H), 3.85 (q, 2H), 4.80 (br, 1H), 7.2 (s, 1H), 7.5 (s, 1H), 6.8-7.8 (m, 6H), 10.1 (br, 1H).

Provenance & Evidence