1-Nitro-2-(2,2,2-trifluoroethoxy)benzene → 2-(2,2,2-trifluoroethoxy)aniline

HRID 342543

Reaction equation

[F:1][C:2]([F:15])([F:14])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11]([O-])=O>O.[Pt]=O.C(O)C>[F:1][C:2]([F:14])([F:15])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH2:11]

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 1-(2,2,2-trifluoroethoxy)-2-nitrobenzene (15 g, 68 mmol), platinum oxide hydrate (100 mg) and absolute ethanol (80 mL) was hydrogenated 18 hours with stirring at 25° C. and 15 psi of pressure. The reaction mixture then was filtered and concentrated. The residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (9:1) to give 2-(2,2,2-trifluoroethoxy)aniline (10.4 g, 54.5 mol), m.p. 49°-50° C.

Workup

filtrationThe reaction mixture then was filtered
concentrationconcentrated
customThe residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (9:1)

Sources & evidence

ORD record: ord-4a164bcad9bc47f79b3cc3d17da470f8
Source dataset: uspto-grants-1999_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05859014

Linked notes

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