Water → Methyl 3-[4-[(4'-chloro-2'-methylbiphenyl-3-yl)methoxy]phenyl]propanoate

HRID 273401

Reaktionsgleichung

Reaktionsgleichung von HRID 273401
Br[C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:9][CH:8]=1.[Cl:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[C:25]([CH3:32])[CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+].O>C(OCC)(=O)C.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.C1(C)C=CC=CC=1.C(O)C>[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([C:2]2[CH:21]=[CH:20][CH:19]=[C:4]([CH2:5][O:6][C:7]3[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:9][CH:8]=3)[CH:3]=2)=[C:25]([CH3:32])[CH:24]=1

Komponenten

9

Edukt 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 5017600(4-Chloro-2-methylphenyl)boronic acidHCID 23136270Methyl 4-[(3-bromophenyl)methoxy]benzenepropanoate

Produkt 1

HCID 58903150Methyl 3-[4-[(4'-chloro-2'-methylbiphenyl-3-yl)methoxy]phenyl]propanoateAusbeute 88,5 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of methyl 3-[4-[(3-bromobenzyl)oxy]phenyl]propanoate (0.5 g, 1.43 mmol), 4-chloro-2-methylphenylboronic acid (0.30 g, 1.72 mmol), tetrakis(triphenylphosphine)palladium(0) (0.083 g, 0.072 mmol), sodium carbonate (0.46 g, 4.29 mmol), water (5 mL), ethanol (5 mL) and toluene (25 mL) was stirred under an argon atmosphere at 90° C. for 16 hrs. The reaction mixture was cooled, diluted with ethyl acetate, washed with water and saturated brine, dried and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-4/1) to give the title compound (0.50 g, yield 88%) as a colorless oil.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. washwashed with water and saturated brine
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-4/1)

Quellen und Nachweise

ORD-Eintrag
ord-cbe6b4fbe9b945ec9dd0c15d5272c25b
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456218B2

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