1,1-Dimethylethyl N-(2-fluoro-6-methylphenyl)carbamate → 2-Fluoro-6-methylaniline

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Reaction Steps

The crude carbamate from step 2 (7.2 g, 32 mmol) was treated with trifluoroacetic acid (30 mL). The resulting solution was stirred at room temperature for 30 minutes, then most of trifluoroacetic acid was evaporated under vacuum. The residue was diluted with CH2Cl2 and poured into a slurry of solid Na2CO3 in CH2Cl2. The resulting slurry was carefully treated with EtOAc to increase product solubility, then filtered through a pad of silica gel and the product washed off with EtOAc. The filtrate and washings were concentrated under vacuum to afford 2-fluoro-6-methylaniline as a yellow solid.

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