Ammonium Chloride → 3-Chloro-4-(3-fluorobenzyloxy)aniline

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To a solution of 2-chloro-1-[(3-fluorobenzyl)oxy]-4-nitrobenzene from Example 3A (8.70 g, 25.1 mmol) in ethanol (150 mL) was added zinc powder (10.1 g, 154 mmol), and the mixture was heated to 60° C. A solution of ammonium chloride (3.30 g, 61.8 mmol) in water (30 mL) was added dropwise, and the reaction was stirred for additional 2 h at this temperature. The mixture was filtered through Celite®, and the solvent was removed in vacuo. The residue was triturated with water, and the precipitate was collected by suction filtration, washed with water and dried to yield 7.63 g (98%) of the aniline.

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