Triethylamine → 1-Chloro-2,4-difluoro-5-nitrobenzene

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Reaction Steps

A solution of 2,6-difluoro-5-chloronitrobenzene (2.0g., 1.03 × 10-2 mole) and triethylamine (2.1g., 2.06 × 10-2 mole) was hydrogenated over 10% palladium carbon catalyst for 18 minutes at room temperature and for an additional 4 hours at 60° C. The catalyst was removed by filtration and washed twice with methanol, using 16 ml. of each wash. The solvent was evaporated and the residue was treated with dichloromethane. The resulting mixture was washed with 15 ml. of water, 70 ml. of ammonium hydroxide solution and then 15 ml. of water, and dried over Na2SO4. Evaporation of the remaining solvent gave 1.25 g. of a yellow oil, a yield of 94%. Gas chromatography established the reaction product to contain 89.5% 2,4-difluoro-aniline.

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