3-Phenoxyaniline → 3-[(n-3-Phenoxy-phenyl)amino]1,1,1-trifluoro-2-propanol

HRID 48045

Reaktionsgleichung

Reaktionsgleichung von HRID 48045
[O:1]([C:8]1[CH:9]=[C:10]([CH:12]=[CH:13][CH:14]=1)[NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:15][C:16]([F:21])([F:20])[CH:17]1[O:19][CH2:18]1>>[O:1]([C:8]1[CH:9]=[C:10]([NH:11][CH2:18][CH:17]([OH:19])[C:16]([F:21])([F:20])[F:15])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

3

Edukt 2

HCID 771353-PhenoxyanilineHCID 5207692-(Trifluoromethyl)oxirane

Produkt 1

HCID 235060633-[(n-3-Phenoxy-phenyl)amino]1,1,1-trifluoro-2-propanolAusbeute 71 %

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Ex-588B) A mixture of solid 3-phenoxyaniline (2.96 g, 16 mmol) and 1,1,1-trifluoro-2,3-epoxypropane (1.30 mL, 15.0 mmol) was placed in a sealed tube and heated to 100° C. giving a dark solution. The stirred solution was heated 18 h and cooled to give a dark oil. Purification by flash chromatography on silica gel eluting with dichloromethane gave 3.15 g (71%) of the desired 3-[(N-3-phenoxy-phenyl)amino]-1,1,1-trifluoro-2-propanol product as a colorless oil. Anal. calcd. for C15H14NO2F3.0.05 CH2Cl2: C, 59.92; H, 4.71; N, 4.64. Found: C, 59.92; H, 4.53; N, 4.73. HRMS calcd. 298.1055 [M+H]+, found: 298.1056.

Aufarbeitung

  1. customwas placed in a sealed tube
  2. customgiving a dark solution
  3. temperatureThe stirred solution was heated 18 h
  4. temperaturecooled
  5. customto give a dark oil
  6. customPurification by flash chromatography on silica gel eluting with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-7cc77ebebe164d0780842c4363c5a42a
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06699898B2

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