Potassium Fluoride → 4-[1-(4'-Isopropyl-2,6-dimethyl-biphenyl-4-yloxy)-2-methyl-propyl]-benzoic acid methyl ester

HRID 1914341Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1914341
[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([O:14][C:15]2[CH:20]=[C:19]([CH3:21])[C:18](Br)=[C:17]([CH3:23])[CH:16]=2)[CH:11]([CH3:13])[CH3:12])=[CH:6][CH:5]=1.[F-].[K+].[CH:27]([C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1)([CH3:29])[CH3:28]>>[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([O:14][C:15]2[CH:20]=[C:19]([CH3:21])[C:18]([C:33]3[CH:34]=[CH:35][C:30]([CH:27]([CH3:29])[CH3:28])=[CH:31][CH:32]=3)=[C:17]([CH3:23])[CH:16]=2)[CH:11]([CH3:13])[CH3:12])=[CH:6][CH:5]=1

Komponenten

4

Edukt 3

HCID 522689Potassium FluorideHCID 27734804-Isopropylphenylboronic acidHCID 671534754-[1-(4-Bromo-3,5-dimethyl-phenoxy)-2-methyl-propyl]-benzoic acid methyl ester

Produkt 1

HCID 671535504-[1-(4'-Isopropyl-2,6-dimethyl-biphenyl-4-yloxy)-2-methyl-propyl]-benzoic acid methyl esterAusbeute 92,5 %

Versuchsvorschrift

Isomer 1 of 4-[1-(4-bromo-3,5-dimethyl-phenoxy)-2-methyl-propyl]-benzoic acid methyl ester (500 mg, 1.28 mmol), potassium fluoride (223 mg, 3.84 mmol), 4-isopropylphenyl boronic acid (419 mg, 2.56 mmol) and tetrakis-(triphenylphosphine)palladium (148 mg, 0.128 mmol) are placed in a flask. After the reaction is purged with N2 for several times, THF/H2O (20 ml/5 ml) is added. The resulting solution is refluxed overnight, loaded on silica gel, eluted with hexane and ethyl acetate to give the titled compound (510 mg).

Aufarbeitung

  1. customAfter the reaction is purged with N2 for several times, THF/H2O (20 ml/5 ml)
  2. additionis added
  3. temperatureThe resulting solution is refluxed overnight
  4. washeluted with hexane and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-c75c8c189a0648858c8de521e2c1cbf5
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08609892B2

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