Hydrochloric Acid → N-(5-benzyl-2-hydroxyphenyl)-2-fluoro-4-formylbenzamide

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Reaction Steps

To a mixture of 2-fluoro-4-formylbenzoic acid (0.600 g, 3.57 mmol) in 15 mL DCM was added oxalyl dichloride (0.374 mL, 4.28 mmol) and N,N-dimethylformamide (0.00261 g, 0.0357 mmol) (a few drops). The mixture was allowed to stir for several h, treated with additional (COCl)2 (0.100 mL), stirred further for 1 h, concentrated in vacuo, and the semi-solid was suspended in 15 mL THF. N,N-diisopropylethylamine (0.808 mL, 4.64 mmol) was added followed by 2-amino-4-benzylphenol (0.711 g, 3.57 mmol). After 4 h, the reaction was treated with EtOAc, water, and 1N HCl. The organic layer was washed 1× brine, dried over sodium sulfate, filtered, and concentrated. The material was purified by silica gel chromatography to give title compound as a solid. MS (ESI) m/z: Calculated: 349.1; Observed: 347.7 (M−−1).

Provenance & Evidence