4-Chlorophenol → HCID 9906124, compound

Participants

Reaction Steps

To a solution of 4-chlorophenol (2.87 g, 22.3 mmol) in THF (30 mL) at 0° C., 1.0 M solution of ethyl magnesium bromide (22.3 mL, 22.3 mmol) in THF was added dropwise. The resulting white suspension was then concentrated to dryness and dissolved in CH2Cl2 (30 mL). Neat 6-(trifluoromethyl)isatin (4.0 g, 18.6 mmol) was then added at once. After stirring at room temperature for 4 hours, the reaction was quenched with 1N HCl solution. The organic layer was separated, washed with water and brine, dried over MgSO4, and filtered. The filtrate was concentrated in vacuo to provide a dark red oil which was purified by flash column chromatography (silica gel, 1:1 hexanes/EtOAc) to afford the title compound as an orange solid (5.48 g, 86% yield). 1H NMR (DMSO-d6): δ10.61 (s, 1H), 9.73 (s, 1H), 7.73(d, J=2.7 Hz, 1H), 7.15-7.21 (m, 2H), 7.03-7.07 (m, 2H), 6.81 (s, 1H), 6.61 (d, J=8.6 Hz, 1H).

Provenance & Evidence