Toluene → 3-Fluoro-4-phenylmethoxyaniline

HRID 445476Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 445476
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][C:10]=1[F:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.C([O-])=O.[NH4+]>[Fe].O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][C:10]=1[F:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 1140TolueneHCID 2723923Ammonium formateHCID 220309121-(Benzyloxy)-2-fluoro-4-nitrobenzene

Produkt 1

HCID 219518923-Fluoro-4-phenylmethoxyanilineAusbeute 87,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 1-benzyloxy-2-fluoro-4-nitro-benzene (44 g, 178 mmol), toluene (400 ml), ammonium formate (35 g), iron (30 g), and water (400 ml) was heated to reflux with stirring overnight. The reaction mixture was filtered through celite and washed with ethyl acetate (400 ml). The organic layer was separated and washed with brine (300 ml), dried over sodium sulfate and concentrated to give 4-benzyloxy-3-fluoro-phenylamine as an oil (33.7 g, 87%). 1H NMR (400 MHz, CDCl3): δ 7.41-7.29 (m, 5H), 6.79 (t, 1H), 6.45 (dd, 1H), 6.14 (dd, 1H), 5.02 (s, 2H), 3.50 (s, 2H). LC/MS: (M+1) 218.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux
  3. filtrationThe reaction mixture was filtered through celite
  4. washwashed with ethyl acetate (400 ml)
  5. customThe organic layer was separated
  6. washwashed with brine (300 ml)
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d759809edca445149461e1d4267441ae
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476298B2

Notizen zur Reaktion

Wird geladen…