Ethyl Acetate → 3,5-Dichloro-4-(4-fluoro-3-methyl-phenoxy)-nitrobenzene

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A mixture of 3-methyl-4-fluorophenol (99 mg, 0.79 mmol), potassium hydroxide (53 mg, 0.94 mmol), 4-iodo-3,5-dichloro-nitrobenzene (250 mg, 0.79 mmol) and 4A° molecular sieves (75 mg) in N-methylpyrolidinone (3 mL) was stirred at 130° C. for 2 h. The reaction mixture was poured into ice cold 1 N HCl (20 mL) and EtOAc (25 mL) was added. The EtOAc phase was separated and washed with 1N HCl (3×25 mL) and brine (25 mL). The EtOAc solution was dried over Na2SO4, filtered and concentrated. The residue was purified by preparative TLC (Hexanes: CH2Cl2=7:3) to afford 3,5-dichloro-4-(4-fluoro-3-methyl-phenoxy)-nitrobenzene (207 mg). MS Calc.: 315.0 Found: 315.0 (M).

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