Phenol → HCID 58307334, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of [2-(3-fluoro-4-nitro-phenoxy)-ethyl]-dimethyl-amine (2.8 g, 12 mmol) and phenol (1.4 g, 15 mmol) in DMF (100 mL) was treated with potassium carbonate (3.4 g, 25 mmol) and the mixture heated at 110° C. under N2 with stirring. After 4 hours, the mixture was cooled to ambient temperature. The mixture was evaporated in vacuo, and the residue was partitioned between ethyl acetate (100 mL) and water (100 mL), and the aqueous phase was extracted with ethyl acetate (100 mL). The combined organic phases were washed with 10% potassium carbonate (2×100 mL) and water (2×100 mL), and were then extracted with dilute aqueous HCl (3×75 mL). The combined aqueous extracts were washed with CH2Cl2 (2×100 mL), basified (NaOH), and extracted into ethyl acetate (3×75 mL). The combined organic phases were washed with water (2×100 mL), dried (MgSO4) and evaporated, providing 3.1 g, in 84% yield; 1H NMR (CDCl3) δ 2.29 (s, 6H), 2.67 (t, J=5.8 Hz, 2H), 4.00 (t, J=5.8 Hz, 2H), 6.46 (d, J=2.6 Hz, 1H), 6.68 (dd, J=9.2 Hz, J=2.6 Hz, 1H), 7.03-7.07 (m, 2H), 7.18-7.22 (m, 1H), 7.35-7.42 (m, 2H), 8.06 (d, J=9.2 Hz, 1H).

Provenance & Evidence