Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 3-Fluoro-4-(5-(phenylthio)benzo[d]oxazol-2-yl)benzaldehyde

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Reaction Conditions

Reaction Steps

A mixture of 2-fluoro-4-formyl-N-(2-hydroxy-5-(phenylthio)phenyl)benzamide (0.180 g, 0.490 mmol) and pyridinium p-toluenesulfonate (0.123 g, 0.490 mmol) in 5.0 mL toluene was heated to 130° C. in a sealed tube for a total of 6 h. The reaction was cooled and was partitioned between 1N NaOH and EtOAc. The organic layer was washed 1× brine, dried over sodium sulfate, filtered, and concentrated in vacuo to give a solid that was purified by silica gel chromatography, 0-30-60% EtOAc/hexanes to give 3-fluoro-4-(5-(phenylthio)benzo[d]oxazol-2-yl)benzaldehyde as a yellow solid. MS (ESI) m/z: Calculated: 349.1; Observed: 350.0 (M++1).

Provenance & Evidence