Sodium Hydroxide → 2-Amino-6-(trifluoromethyl)phenol

HRID 568030Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 568030
[F:1][C:2]([F:14])([F:13])[C:3]1[C:8]([OH:9])=[C:7]([N+:10]([O-])=O)[CH:6]=[CH:5][CH:4]=1.[Sn](Cl)Cl.[OH-].[Na+]>C(O)C>[NH2:10][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([C:2]([F:1])([F:13])[F:14])[C:8]=1[OH:9]

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 9018342-Nitro-6-(trifluoromethyl)phenol

Produkt 1

HCID 222727462-Amino-6-(trifluoromethyl)phenolAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 6-trifluoromethyl-2-nitrophenol(1.84 g, 8.67 mmol) and tin (II) chloride (6.0 g, 26.2 mmol) in ethanol(150 mL) was heated at 80° C. under argon. After 2 hours, the starting material has disappeared and the solution was allowed to cool down and then poured into ice. The pH was made slightly basic (pH7-8), by addition of solid NaOH, before being extracted with ethyl acetate. The organic phase was washed with brine, dried over MgSO4 and filtered. The solvent was evaporated and chromatography of the resulting solid on silica gel (4% MeOH/CH2Cl2) gave the desired product(1.35 g, 88%). 1H NMR (CD3OD): δ 6.93 (d, 1H), 6.82 (t, 1H), 6.78 (d, 1H).

Aufarbeitung

  1. temperatureto cool down
  2. additionpoured into ice
  3. extractionbefore being extracted with ethyl acetate
  4. washThe organic phase was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-9d63162321954f84acefbe24996014d6
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06180675B2

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