4-Chlorophenol → HCID 68998471, compound

Participants

Reaction Conditions

Reaction Steps

4-chlorophenol (495 mg, 3.85 mmol), the product from step 1 (1 g, 2.57 mmol), cesium carbonate (1.67 g, 5.14 mmol), copper iodide (51 mg, 0.27 mmol), and N,N-dimethylglycine HCl (35 mg, 0.249 mmol), were taken into anhydrous dioxane (12 mL) in a nitrogen flushed 20 mL vial. The reaction was heated to 90° C. for 24 h. The mixture was concentrated to dryness, and the resulting oil was partitioned between water and ethyl acetate. The aqueous layer was washed with ethyl acetate 3×. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated to dryness. The compound was purified by flash column chromatography (20:1 silica ratio, eluted with 20% ethyl acetate in hexane) to obtain the title product (1 g, ˜90%).;LCMS; m/z 390 (M) 88% pure; 1H NMR (400 MHz, DMSO); δ 1.41 (s, 9H), 2.00-2.20 (m, 2H), 3.32-3.60 (m, 4H), 4.98 (s, 1H), 6.76 (d, 2H, J=8.8,), 6.94-7.03 (m, 4H), 7.19 (d, 2H), J=8.8,), 9.70 (s, 1H).

Provenance & Evidence