Toluene → 3-Fluoro-4-phenylmethoxyaniline

HRID 445473Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 445473
C([O-])=O.[NH4+].[CH2:5]([O:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][C:14]=1[F:22])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C1(C)C=CC=CC=1>[Fe].O>[CH2:5]([O:12][C:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][C:14]=1[F:22])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Komponenten

6

Edukt 3

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

Produkt 1

HCID 219518923-Fluoro-4-phenylmethoxyanilineAusbeute 101,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of iron powder (45.2 g, 0.809 g atoms), ammonium formate (53.6 g, 0.850 mol), 1-benzyloxy-2-fluoro-4-nitrobenzene (50.0 g, 0.200 mol), toluene (400 mL) and water (400 mL) was heated to reflux overnight. The mixture was filtered through Celite and washed with hot ethyl acetate. The combined organic layers were washed with water and brine, then dried over sodium sulfate and concentrated to afford 4-benzyloxy-3-fluoroaniline (44 g, 100%). 1H NMR (400 MHz, d6-DMSO): δ 7.43-7.26 (m, 5H), 6.90 (dd, 1H), 6.49 (dd, 1H), 6.34 (m, 1H), 4.99 (br s, 2H), 4.98 (s, 2H); 13C NMR (100 MHz, d6-DMSO): δ 171.1, 155.1, 152.7, 144.9, 138.0, 137.2, 129.6, 129.0, 128.5, 118.9, 110.0, 102.9, 72.5; IR (cm−1): 1510, 1454, 1277, 1215, 1126, 1007, 957, 843, 800, 789, 739, 694, 604; LC/MS (M+H=218).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. filtrationThe mixture was filtered through Celite
  4. washwashed with hot ethyl acetate
  5. washThe combined organic layers were washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3a57777330924072b53206d7e73b45bd
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476298B2

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