Triethylamine → HCID 58444590, Verbindung

HRID 1509766Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1509766
Br[CH:2]1[CH:7]([CH2:8][CH3:9])[CH2:6][O:5][CH:4]([C:10]2[CH:15]=[CH:14][C:13]([B:16]3[O:20][C:19]([CH3:22])([CH3:21])[C:18]([CH3:24])([CH3:23])[O:17]3)=[C:12]([F:25])[CH:11]=2)[CH2:3]1.[H][H].C(N(CC)CC)C>C1(C)C=CC=CC=1.O.[Pd]>[CH2:8]([CH:7]1[CH2:6][O:5][CH:4]([C:10]2[CH:15]=[CH:14][C:13]([B:16]3[O:17][C:18]([CH3:24])([CH3:23])[C:19]([CH3:22])([CH3:21])[O:20]3)=[C:12]([F:25])[CH:11]=2)[CH2:3][CH2:2]1)[CH3:9]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 58444576HCID 58444576, VerbindungHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 58444590HCID 58444590, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 22272177Toluene waterLösungsmittel

Versuchsvorschrift

18.0 g (36.2 mmol) of 4-bromo-5-ethyl-2-[3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]tetrahydropyran are hydrogenated for 30 h at a hydrogen pressure of 5 bar and at 80° C. in toluene/water in the presence of Pd/C (5% of Pd) and 12.7 ml (88.1 mmol) of triethylamine. The organic phase is separated off and filtered absorptively (SiO2, toluene). The filtrate is concentrated to dryness, and the residue is recrystallised from ethanol at reduced temperature, giving 5-ethyl-2-[3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]tetrahydropyran as a colourless solid.

Aufarbeitung

  1. customThe organic phase is separated off
  2. filtrationfiltered absorptively (SiO2, toluene)
  3. concentrationThe filtrate is concentrated to dryness
  4. customthe residue is recrystallised from ethanol at reduced temperature

Quellen und Nachweise

ORD-Eintrag
ord-2b094232b48642f2a451f1a7b0685be9
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08211513B2

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