Hydrochloric Acid → 4-(1-Ethoxy-2-methylpropan-2-yl)-3,5-difluoroaniline

A mixture of 4-(1-ethoxy-2-methylpropan-2-yl)-3,5-difluoro-N,N-bis(4-methoxybenzyl)aniline (8.51 g, 18.12 mmol), 1N hydrochloric acid (36.2 mL) and 10% palladium-carbon (1.929 g, 0.91 mmol, 50%, wet) in MeOH (164 mL) under hydrogen atmosphere (4 atm), and the mixture was stirred at room temperature for 1.5 hr. The catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure. The obtained residue was dissolved in ethyl acetate, and the solution was washed with 1N aqueous sodium hydroxide solution and brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 5→20% ethyl acetate/hexane) to give 4-(1-ethoxy-2-methylpropan-2-yl)-3,5-difluoroaniline (3.87 g, 16.88 mmol, 93%) as a white solid.

1. customThe catalyst was removed by filtration
2. concentrationthe filtrate was concentrated under reduced pressure
3. dissolutionThe obtained residue was dissolved in ethyl acetate
4. washthe solution was washed with 1N aqueous sodium hydroxide solution and brine
5. dry with materialdried over magnesium sulfate
6. customthe solvent was evaporated under reduced pressure
7. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 5→20% ethyl acetate/hexane)

ORD record

ord-976ff95b173a4142a13170aefcab8f65

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09365520B2