(1,1'-Biphenyl)-2-ol → HCID 66845232, compound

Participants

Reaction Conditions

Reaction Steps

Copper(I) iodide (69.4 mg, 0.364 mmol), 2-phenylphenol (93.0 mg, 0.546 mmol) and cesium carbonate (1.78 g, 5.46 mmol) were added to a dry flask under nitrogen. Ethyl malonate (1.11 mL, 7.29 mmol) was added to the mixture, followed by 1-chloro-2,5-difluoro-4-iodobenzene (1.00 g, 3.64 mmol) in tetrahydrofuran (3.64 mL, 44.9 mmol). The reaction mixture was sealed and heated to 90° C. After 12 hours, the reaction mixture was allowed to cool to room temperature and then diluted with saturated NH4Cl and EtOAc. The organic layer was separated, dried and filtered through Celite. The brown oil was purified via silica gel chromatography (0-30% EtOAc-hexane) to give diethyl 2-(4-chloro-2,5-difluorophenyl)malonate (0.65 g, 58%). 1H NMR (400 MHz, CDCl3) δ 7.37 (dd, J=6.3, 9.3, 1H), 7.17 (dd, J=6.1, 8.9, 1H), 4.91 (s, 1H), 4.33-4.14 (m, 4H), 1.28 (t, J=7.2, 6H).

Provenance & Evidence