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Potassium Fluoride → Methyl 2'-methyl-2-(methylsulfonyl)biphenyl-4-carboxylate

HRID 219830
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 219830
Cl[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[S:12]([CH3:15])(=[O:14])=[O:13].[C:16]1([CH3:25])[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1B(O)O.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.[F-].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.CO.C1(C)C=CC=CC=1>[CH3:25][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[S:12]([CH3:15])(=[O:14])=[O:13]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 522689Potassium FluorideHCID 27332672-Methylphenyl boronic acidHCID 10490815Methyl 4-chloro-3-(methylsulfonyl)benzoateHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl

Produkt 1

HCID 67528382Methyl 2'-methyl-2-(methylsulfonyl)biphenyl-4-carboxylateAusbeute 88,7 %

Reagenzien, Katalysatoren, Lösungsmittel

4
HCID 167845palladium(II) acetateKatalysatorHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

In a schlenk flushed with Argon were added methyl 4-chloro-3-(methylsulfonyl)benzoate (124.34 mg; 0.50 mmol; 1 eq.), o-tolylboronic acid (84.97 mg; 0.62 mmol; 1.25 eq.), palladium(II) acetate (22.45 mg; 0.10 mmol; 0.20 eq.), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (82.11 mg; 0.20 mmol; 0.40 eq.), potassium fluoride (87.14 mg; 1.50 mmol; 3 eq.), toluene (2.49 mL), MeOH (2.49 mL) and water (5.40 μl). The reaction was degassed with Ar and heated under reflux for 2 hours. Then, it was cooled down to RT. The solvents were evaporated and the crude mixture was dissolved in EtOAc, washed with water and brine and dried over MgSO4. The resulting crude product was purified by flash chromatography (c-hex/EtOAc 9:1 to 5:5), affording the title compound as a light yellow oil (135 mg; 88%). 1H NMR (DMSO-d6, 300 MHz) δ 8.89 (d, J=1.77 Hz, 1H), 8.32 (dd, J=1.77, 7.90 Hz, 1H), 7.43-7.19 (m, 5H), 4 (s, 3H), 2.76 (s, 3H), 2.09 (s, 3H). LC/MS (Method B): 305.1 (M+H)+. HPLC (max plot) 99.2%; Rt 4.51 min.

Aufarbeitung

  1. customIn a schlenk flushed with Argon
  2. customThe reaction was degassed with Ar
  3. temperatureheated
  4. temperatureunder reflux for 2 hours
  5. customThe solvents were evaporated
  6. dissolutionthe crude mixture was dissolved in EtOAc
  7. washwashed with water and brine
  8. dry with materialdried over MgSO4
  9. customThe resulting crude product was purified by flash chromatography (c-hex/EtOAc 9:1 to 5:5)

Quellen und Nachweise

ORD-Eintrag
ord-1f2d047105c649f6b7e09107e97eb42e
Quelldatensatz
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08202865B2

Notizen zur Reaktion

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