Sodium Hydroxide → 4-({[1-Bromo-6-(2-phenyl-1,3-thiazol-4-yl)-2-naphthyl]oxy}methyl)benzoic acid

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Reaction Steps

A mixture of methyl 4-({[1-bromo-6-(2-phenyl-1,3-thiazol-4-yl)-2-naphthyl]oxy}methyl)benzoate (214.8 mg, 0.405 mmol), prepared in the previous step, and 1 N NaOH (608 μL, 0.608 mmol) in 40 mL of THF plus 40 mL of methanol plus 10 mL of water was refluxed for 24 h. By TLC starting material remained. An additional 608 μL (0.608 mmol) of 1 N NaOH was added and the mixture refluxed for 24 h. After cooling to room temperature the reaction was filtered, acidified by the addition of 5 mL of 1 N HCl and then concentrated under reduced pressure to remove the THF and methanol. The solid present was collected by filtration, washed with water and dried under reduced pressure to give the title compound (152.9 mg, 73%) as a white solid, mp 268-270° C. Elemental analysis for C27H18BrNO3S.0.20H2O Calc'd: C, 62.36; H, 3.57; N, 2.69. Found: C, 62.38; H, 3.54; N, 2.62.

Provenance & Evidence