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Cesium fluoride → Methyl 3'-fluoro-2-(methoxymethyl)-2'-methylbiphenyl-4-carboxylate

HRID 2410472
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2410472
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH2:12][O:13][CH3:14].[F:15][C:16]1[C:17]([CH3:34])=[C:18](C2C=CC(C(O)=O)=CC=2COC)[CH:19]=[CH:20][CH:21]=1.FC1C(C)=C(B(O)O)C=CC=1.[F-].[Cs+]>O1CCOCC1.CC(OC)(C)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[F:15][C:16]1[C:17]([CH3:34])=[C:18]([C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=2[CH2:12][O:13][CH3:14])[CH:19]=[CH:20][CH:21]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 25953Cesium fluorideHCID 27831913-Fluoro-2-methylphenylboronic AcidHCID 580663983'-Fluoro-2-(methoxymethyl)-2'-methylbiphenyl-4-carboxylic acidHCID 58554220Methyl 4-bromo-3-(methoxymethyl)benzoate

Produkt 1

HCID 58554131Methyl 3'-fluoro-2-(methoxymethyl)-2'-methylbiphenyl-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 15413tert-Butyl methyl etherLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of methyl 4-bromo-3-(methoxymethyl)benzoate (Intermediate 1, Step 2, 5.00 g, 19.3 mmol), 3-fluoro-2-methylphenylboronic acid (4.46 g, 29.0 mmol), bis(triphenylphosphine)palladium(II) chloride (271 mg, 0.39 mmol) and cesium fluoride (8.79 g, 57.9 mmol) was prepared in dioxane (50 mL) and water (20 mL) under nitrogen atmosphere. The reaction mixture was heated at 100° C. for 1 hour. The reaction mixture was cooled at RT, diluted with MTBE (250 mL) and the layers were separated. The organic layer was washed with water (100 mL) and brine (100 mL). The aqueous layers were extracted with MTBE (150 mL). The organic layers were combined, dried over MgSO4 and concentrated under reduced pressure. After purification by flash chromatography (silica, EtOAc/n-hexane), the title compound was obtained as a colorless oil (4.85 g, 87%). HPLC (Method A), Rt 5.0 min (purity: 99.5%). LC/MS (Method B): 289.0 (M+H)+.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled at RT
  2. customthe layers were separated
  3. washThe organic layer was washed with water (100 mL) and brine (100 mL)
  4. extractionThe aqueous layers were extracted with MTBE (150 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customAfter purification by flash chromatography (silica, EtOAc/n-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-0cf5d2f1c2c84bc3b2a455209f39cd07
Quelldatensatz
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08815919B2

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