Hydrochloric Acid → 1-Fluoro-3-methoxy-2-(3-nitro-phenoxy)-benzene

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To a 250 mL pressure resistant vial which contained a mixture of 2-fluoro-6-methoxy-phenol (1000 mg, 7 mmole), 1-iodo-3-nitro-benzene (2500 mg, 10 mmole), Cs2CO3 (1200 mg, 7 mmole) and N,N-dimethylglycine.HCl (200 mg, 1.5 mmole) in dioxane (40 mL) was added CuI (140 mg, 0.7 mmole) at rt. The reaction mixture was bumbled with Ar for 5 min at rt and then the vial was sealed. The reaction mixture was stirred and heated to 98° C. for 5 d. After cooling to rt, the reaction mixture was poured into 250 mL ice-water which was extracted with ethyl acetate (3×50 mL), washed with water (2×50 mL), brine (50 mL) and dried over Na2SO4. After removal of solvent, the residue was purified by silica gel column chromatography with ethyl acetate/hexane as eluent to give 1450 mg (75% yield) of product (10).

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