Hydrochloric Acid → 3-(3-Chloro-phenoxy)-4-methoxy-benzaldehyde

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To a 250 mL pressure resistant vial which contained a mixture of 3-hydroxy-4-methoxy-benzaldehyde (1520 mg, 10 mmole), 1-Iodo-3-chloro-benzene (2390 mg, 10 mmole), Cs2CO3 (1600 mg, 10 mmole) and N,N-dimethylglycine.HCl (280 mg, 2 mmole) in dioxane (40 mL) was added CuI (380 mg, 2 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 heated to 98° C. and stirred for 24 h and then 110° C. for 20 h. After cooling to rt, the reaction mixture was poured onto 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 500 mg (24% yield) of product (12).

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