Hydrochloric Acid → HCID 68481886, Verbindung

HRID 1191584Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1191584
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1B(O)O.Br[C:13]1[CH:14]=[CH:15][C:16]([CH2:32][CH3:33])=[C:17]([CH:19]2[C:24](=[O:25])[C:23]([CH3:27])([CH3:26])[C:22](=[O:28])[C:21]([CH3:30])([CH3:29])[C:20]2=[O:31])[CH:18]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].Cl>ClCCl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[Na].[Na].[Na].S(C1C=C(P(C2C=CC=C(S(O)(=O)=O)C=2)C2C=CC=C(S(O)(=O)=O)C=2)C=CC=1)(O)(=O)=O.O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:13]1[CH:14]=[CH:15][C:16]([CH2:32][CH3:33])=[C:17]([CH:19]2[C:20](=[O:31])[C:21]([CH3:29])([CH3:30])[C:22](=[O:28])[C:23]([CH3:27])([CH3:26])[C:24]2=[O:25])[CH:18]=1

Komponenten

9

Edukt 4

HCID 313Hydrochloric AcidHCID 62657Potassium Phosphate, Tribasic2×HCID 2734659(2,4-Dichlorophenyl)boronic acid2×HCID 684845366-(5-Bromo-2-ethylphenyl)-2,2,4,4-tetramethylcyclohexane-1,3,5-trione

Produkt 1

HCID 68481886HCID 68481886, VerbindungAusbeute 37,4 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 167845palladium(II) acetateKatalysatorHCID 86657037CID 86657037KatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

To a microwave vial is added palladium(II) acetate (1.1 mg, 0.0049 mmol), tris(3-sulfophenyl)phosphine trisodium salt (5.1 mg, 0.0099 mmol), 2,4-dichlorophenylboronic acid (0.099 g, 0.5 mmol), 6-(5-bromo-2-ethylphenyl)-2,2,4,4-tetramethylcyclohexane-1,3,5-trione (0.19 g, 0.5 mmol) and potassium phosphate (0.53 g, 2.5 mmol). Degassed water (0.75 ml) is next added (washing-down any solids from the slides of the vial), followed by stirring for 5 minutes and flushing with argon. This mixture is then heated at 160° C. under microwave irradiation for 15 minutes. A further quantity of 2,4-dichlorophenylboronic acid (0.099 g, 0.5 mmol) and potassium phosphate (0.095 g, 0.5 mmol) are added, the reaction mixture again blanketed under an atmosphere of argon, and the mixture is heated at 160° C. for a further 15 minutes. After cooling to room temperature the reaction mixture is diluted with dichloromethane (5 ml) and acidified with 2M aqueous hydrochloric acid. The organic phase is separated, dried over anhydrous magnesium sulfate, and filtered through a plug of silica gel. The filtrate is concentrated under reduced pressure and the residue is dissolved in N,N-dimethylformamide (approximately 1 ml) and purified by preparative reverse phase HPLC to afford 6-(2′,4′-dichloro-4-ethylbiphenyl-3-yl)-2,2,4,4-tetramethyl-cyclohexane-1,3,5-trione as a colourless oil (80.6 mg).

Aufarbeitung

  1. washwashing-down any solids from the slides of the vial),
  2. customflushing with argon
  3. temperaturethe mixture is heated at 160° C. for a further 15 minutes
  4. temperatureAfter cooling to room temperature the reaction mixture
  5. customThe organic phase is separated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered through a plug of silica gel
  8. concentrationThe filtrate is concentrated under reduced pressure
  9. dissolutionthe residue is dissolved in N,N-dimethylformamide (approximately 1 ml)
  10. custompurified by preparative reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-de338d87e4f94b4a8fcc54a993467cfd
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680012B2

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