2,4-Dichlorophenol → 2,4-Dichloro-1-(2-nitrophenoxy)benzene

Participants

Reaction Steps

Previously described: Burnistov, S. I.; Karpishchenko, L. S. Izvestiya Vysshikh Uchebnykh Zavedenii, Khimiya i Khimicheskaya Tekhnologiya 1976, 19(1), 39-41. Commercially available Literature mp: 57-58° C. 69-69.6° C. AMR01025 A mixture of 2,4-dichlorophenol (2.00 g, 12.27 mmol), 1-fluoro-2-nitrobenzene (2.07 g, 14.72 mmol) and potassium carbonate (2.04 g, 14.72 mmol) in dimethylformamide (DMF, 10 mL) was stirred under reflux for 1.5 h. After removal of DMF, the residue was dissolved in DCM and washed with NaOH (5%, 3×20 mL) and brine. The organic layer was dried (MgSO4), filtered and evaporated. Flash chromatography on silica gel of the crude product using DCM as eluent gave 1-(2,4-dichlorophenoxy)-2-nitrobenzene (3.4 g, 97%) as a cream oil. Rf: 0.73 (DCM) 1H NMR (270 MHz, CDCl3) δ 6.85 (1H, dd, J=8.4, 1.2 Hz), 6.97 (1H, d, J=8.9 Hz), 7.23 (2H, m), 7.48 (1H, d, J=2.5 Hz), 7.51 (1H, m) and 7.98 (1H, dd, J=8.2, 1.7 Hz). AMR01043 Following the same procedure, from 2,4-dichlorophenol (3.00 g, 18.40 mmol), 1-fluoro-2-nitrobenzene (2.60 g, 18.40 mmol) and potassium carbonate (2.54 g, 18.40 mmol) in dimethylformamide (DMF, 15 mL), and after a reaction time of 3 h, gave AMR01043 (4.89 g, 93%) as a cream solid, mp: 51-54° C.

Provenance & Evidence