Cesium carbonate → HCID 67468254, Verbindung

HRID 2171163Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2171163
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([O:10][CH:11]([F:13])[F:12])[C:3]=1[O:14][CH2:15][O:16][CH3:17].C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C(C)(C)OB([C:32]2[CH:40]=[CH:39][CH:38]=[C:37]3[C:33]=2[CH2:34][CH2:35][C:36]3=[O:41])O1>CN(C)C=O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:12][CH:11]([F:13])[O:10][C:4]1[C:3]([O:14][CH2:15][O:16][CH3:17])=[C:2]([C:32]2[CH:40]=[CH:39][CH:38]=[C:37]3[C:33]=2[CH2:34][CH2:35][C:36]3=[O:41])[CH:7]=[CH:6][C:5]=1[O:8][CH3:9]

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 220320882,3-Dihydro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-inden-1-oneHCID 67465272HCID 67465272, Verbindung

Produkt 1

HCID 67468254HCID 67468254, VerbindungAusbeute 51,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A solution of 1-bromo-3-(difluoromethoxy)-4-methoxy-2-(methoxymethoxy)benzene (3 g, 9.58 mmol) in dimethylformamide (50 mL) was purged with argon for 1 h, to this cesium carbonate (9.34 g, 28.74 mmol), tetrakis(triphenylphosphine) palladium (0) (1.1 g, 0.958 mmol) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-inden-1-one (2.96 g, 11.49 mmol) were added and the resultant reaction mixture was heated to 80° C. for 4 h. The reaction mixture was cooled to RT and filtered and the filtrate was diluted with water and extracted with ethyl acetate (3×). The combined ethyl acetate layers were washed with brine and dried over anhydrous sodium sulphate and concentrated under reduced pressure. Purification by column chromatography (silica gel, 0-20% ethyl acetate in pet ether) afforded 4-(3-(Difluoromethoxy)-4-methoxy-2-(methoxymethoxy)phenyl)-2,3-dihydro-1H-inden-1-one as a solid (1.8 g, 51.6%).

Aufarbeitung

  1. additionwere added
  2. customthe resultant reaction mixture
  3. temperatureThe reaction mixture was cooled to RT
  4. filtrationfiltered
  5. additionthe filtrate was diluted with water
  6. extractionextracted with ethyl acetate (3×)
  7. washThe combined ethyl acetate layers were washed with brine
  8. dry with materialdried over anhydrous sodium sulphate
  9. concentrationconcentrated under reduced pressure
  10. customPurification by column chromatography (silica gel, 0-20% ethyl acetate in pet ether)

Quellen und Nachweise

ORD-Eintrag
ord-e159e49cc45d4a5d840cf250215b7476
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09051290B2

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