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General Procedure for the Synthesis of 5a-p To CH 2Cl2 solution (4 mL) of 3a-e (2.0 mmol) and of 4a-i (2.0 mmol) was added TiCl4 (2.0 mmol) at -78 °C under argon atmosphere. The temperature of the solution was allowed to rise to 20 °C during 20 h. The solution was poured into an aq solution of HCl (10, The organic and the aqueous layer were separated and the latter was extracted (3x) with CH2Cl2. The combined organic layers were dried (Na2SO4, filtered, and the filtrate was concentrated in vacuo. The residue was purified by column chromatography (SiO2, heptane-EtOAc =10:1, Methyl 6-(Dichlorofluoromethyl)-2-hydroxy-3- methoxybenzoate (5b) Starting with 3a (370 mg, 2.0 mmol, 4b (581 mg, 2.0 mmol, and TiCl4 (380 mg, 2.0 mmol, 5b was isolated as a colorless oil (261 mg, 50, mp 50-51 °C; R f= 0.78 n
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35Cl]: 266.01519; found: 266.015398.
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