Yield:-

Reaction Conditions:

with potassium carbonate in acetone for 3 h;Reflux;

Steps:

2-Chloro-4-ethoxy-1-fluorobenzene A mixture of 3-chloro-4-fluorophenol (2.0 g, 13.7 mmol), diethylsulfate (1.58 mL, 17.8 mmol) and K₂CO₃ (9.4 g, 68.5 mmol) in acetone (20 mL) was heated under refluxed for 3 h. The reaction mixture was filtered and concentrated. The residue was diluted with ethyl acetate (50 mL), washed with water (30 mL) and brine. The organic layer was dried (Na₂SO₄) and concentrated to give the title compound as a liquid. ¹H NMR (CDCl₃, 400 MHz): δ=1.39 (t, 3H, J=7.2 Hz), 3.97 (q, 2H, J=7.2 Hz), 6.71-6.74 (m, 1H), 6.89-6.91 (m, 1H), 7.02 (t, 1H, J=8.8 Hz).

References:

OSI Pharmaceuticals, LLC US2011/281888, 2011, A1 Location in patent:Page/Page column 24