Potassium Carbonate → 2,3,4,5,5',6-Hexafluoro-2'-methoxy-1,1'-biphenyl

HRID 1847100

Reaktionsgleichung

Reaktionsgleichung von HRID 1847100
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6](B(O)O)[CH:7]=1.I[C:14]1[C:19]([F:20])=[C:18]([F:21])[C:17]([F:22])=[C:16]([F:23])[C:15]=1[F:24].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:20][C:19]1[C:18]([F:21])=[C:17]([F:22])[C:16]([F:23])=[C:15]([F:24])[C:14]=1[C:6]1[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[O:11][CH3:12]

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 70008PentafluoroiodobenzeneHCID 27826735-Fluoro-2-methoxyphenylboronic acid

Produkt 1

HCID 867104532,3,4,5,5',6-Hexafluoro-2'-methoxy-1,1'-biphenylAusbeute 277,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

Compound 1 (6.3 g, 3.7 mmol, 1 equiv) and iodopentafluorobenzene (5.5 mL, 4 mmol, 1.2 equiv) were dissolved in toluene (120 mL). 1.0 M Potassium carbonate solution (120 mL), tetrabutylammonium bromide (600 mg), and tetrakis(triphenylphosphine)palladium(0) (2.1 g, 1.8 mmol, 0.05 equiv) were added. Nitrogen was sparged through the mixture for 10 minutes. The reaction was refluxed 18 hours, then cooled to room temperature. The layers were separated and the aqueous layer was extracted with methyl tert-butyl ether (2×50 mL). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure. The residue was purified over silica gel (100 g), eluting with a gradient of 0 to 4% ethyl acetate in heptane to give 2,3,4,5,5′,6-hexafluoro-2′-methoxy-1,1′-biphenyl (2) (3.0 g, 28% yield) as an off-white solid.

Aufarbeitung

  1. customNitrogen was sparged through the mixture for 10 minutes
  2. temperatureThe reaction was refluxed 18 hours
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with methyl tert-butyl ether (2×50 mL)
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified over silica gel (100 g)
  8. washeluting with a gradient of 0 to 4% ethyl acetate in heptane

Quellen und Nachweise

ORD-Eintrag
ord-9428941c0fc94688951be6ebf416a85b
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952114B2

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