Potassium Carbonate → 1-Benzyl-4-chloro-2-methoxybenzene

HRID 272744Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 272744
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][C:4]=1[O:10][CH3:11].[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:2]([C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][C:4]=1[O:10][CH3:11])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 223274741-(Bromomethyl)-4-chloro-2-methoxybenzene

Produkt 1

HCID 692167101-Benzyl-4-chloro-2-methoxybenzeneAusbeute 18,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

1-Bromomethyl-4-chloro-2-methoxy-benzene (50 mg, 0.21 mmol), phenyl boronic acid (28 mg, 0.23 mmol), Pd(PPh3)4 (24 mg, 0.021 mmol) and K2CO3 (87 mg, 0.63 mmol) were combined in dioxane, purged with N2, and heated to reflux for 16 hours. The mixture was then partitioned between ethyl acetate and water. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel eluting with 4:1 hexanes/ethyl acetate to provide 9 mg (18%) of the title compound. MS (ESI) m/e 233 (M+H)+.

Aufarbeitung

  1. custompurged with N2
  2. temperatureheated
  3. temperatureto reflux for 16 hours
  4. customThe mixture was then partitioned between ethyl acetate and water
  5. washThe organic layer was washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customThe residue was purified by flash column chromatography on silica gel eluting with 4:1 hexanes/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-cd67fa8b66294287b5b57e87a2dce8c8
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456169B2

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