Bis(trifluoroacetoxy)iodobenzene → 4-[[3-Methyl-4-(4-trifluoromethylbenzyloxy)phenyl]sulfanyl]-2-propylphenoxy-acetic acid ethyl ester

HRID 985042

Reaktionsgleichung

Reaktionsgleichung von HRID 985042
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([SH:13])=[CH:9][C:8]=1[CH2:14][CH2:15][CH3:16])[CH3:2].[CH3:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=1.FC(F)(F)C(OI(C1C=CC=CC=1)OC(=O)C(F)(F)F)=O>FC(F)(F)C(O)C(F)(F)F>[CH2:1]([O:3][C:4](=[O:17])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13][C:23]2[CH:22]=[CH:21][C:20]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][C:30]([C:33]([F:34])([F:36])[F:35])=[CH:29][CH:28]=3)=[C:19]([CH3:18])[CH:24]=2)=[CH:9][C:8]=1[CH2:14][CH2:15][CH3:16])[CH3:2]

Komponenten

5

Edukt 3

HCID 102317Bis(trifluoroacetoxy)iodobenzeneHCID 112193212-[4-(Trifluoromethyl)benzyloxy]tolueneHCID 207681114-Mercapto-2-propylphenoxy-acetic acid ethyl ester

Produkt 1

HCID 591291244-[[3-Methyl-4-(4-trifluoromethylbenzyloxy)phenyl]sulfanyl]-2-propylphenoxy-acetic acid ethyl esterAusbeute 59,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 135291,1,1,3,3,3-Hexafluoro-2-propanolLösungsmittel

Versuchsvorschrift

Compound 4.4 (5.0 g, 19.66 mmol) was dissolved in 1,1,1,3,3,3-hexafluoro-2-propanol (30 mL) under argon atmosphere. To the solution was added compound 4.1 (5.23 g, 19.66 mmol) and [bis(trifluoroacetoxy)iodo]benzene (10.14 g, 23.59 mmol) slowly, while maintaining the reaction temperature between 10° C. and 17° C. After stirring for 15 min, the reaction mixture was concentrated in vacuo to give a residue which was purified using silica gel column chromatography (hexane/EtOAc=20/1) to give 4.5 (6.11 g). 1H NMR (400 MHz) (CDCl3) δ 7.64 (2H, d, J=8.2 Hz); 7.54 (2H, d, J=8.1 Hz); 7.20-7.06 (4H, m); 6.76 (1H, d, J=8.4 Hz); 6.62 (1H, d, J=8.4 Hz); 5.11 (2H, s); 4.60 (2H, s); 4.25 (2H, q, J=7.1 Hz); 2.63-2.56 (2H, m); 2.24 (3H, s); 1.67-1.55 (2H, m); 1.28 (3H, t, J=7.1 Hz); 0.92 (3H, t, J=7.4 Hz).

Aufarbeitung

  1. temperaturewhile maintaining the reaction temperature between 10° C. and 17° C
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. customto give a residue which
  4. customwas purified

Quellen und Nachweise

ORD-Eintrag
ord-38d2925e64434a719c7daf17bfbbfdea
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06869975B2

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