Trifluoroacetic acid → 5-Chloro-3-iodo-2-methylaniline

To a solution of 1,1-dimethylethyl (5-chloro-3-iodo-2-methylphenyl)carbamate (5 g, 13.6 mmol) in dichloromethane (50 mL) was added trifluoroacetic acid (10 mL). The solution was stirred at ambient temperature for 2 hours, then concentrated in-vacuo. The resultant residue was partitioned between saturated sodium bicarbonate and ethyl acetate. The aqueous portion was extracted twice with ethyl acetate. The combined organic portions were washed with brine, dried over sodium sulfate, filtered and concentrated in-vacuo to afford an orange residue which was purified by column chromatography (silica gel, 5% ethyl acetate in hexane). The product was isolated to afford 3.05 g, 11.4 mmol (84%) of 5-chloro-3-iodo-2-methylaniline as a yellow solid. 1H NMR (400 MHz, CDCl3): 7.26 (d, 1H), 6.64 (d, 1H), 3.78 (br s, 2H), 2.28 (s, 3H); MS (EI) for C7H7Cl1N: 268 (MH+).

1. concentrationconcentrated in-vacuo
2. customThe resultant residue was partitioned between saturated sodium bicarbonate and ethyl acetate
3. extractionThe aqueous portion was extracted twice with ethyl acetate
4. washThe combined organic portions were washed with brine
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated in-vacuo
8. customto afford an orange residue which
9. customwas purified by column chromatography (silica gel, 5% ethyl acetate in hexane)
10. customThe product was isolated

ORDレコード

ord-8e9dac0c98d840399d69a8542c6a9630

出典データセット

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08697737B2