Methyl 4-(1-bromo-6-methoxynaphthalen-2-yl)benzoate → Methyl 4-(6-methoxy-1-methylnaphthalen-2-yl)benzoate

HRID 1771459

Reaktionsgleichung

Reaktionsgleichung von HRID 1771459
Br[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=1.[CH3:24][Zn]Cl>C1COCC1.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>[CH3:13][O:12][C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[C:2]([CH3:24])=[C:3]([C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=1)[CH:4]=[CH:5]2

Komponenten

5

Edukt 2

HCID 67974719Methyl 4-(1-bromo-6-methoxynaphthalen-2-yl)benzoateHCID 178477798HCID 178477798, Verbindung

Produkt 1

HCID 67974968Methyl 4-(6-methoxy-1-methylnaphthalen-2-yl)benzoateAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of methyl 4-(1-bromo-6-methoxynaphthalen-2-yl)benzoate (300 mg, 0.811 mmol) (see Example 12 step 1), MeZnCl (1.2 mL, 2.40 mmol, 2M in THF) and Pd(PPh3)4 (93.8 mg, 0.0811 mmol) in anhydrous THF (10 mL) was stirred at 60° C. under N2 atmosphere for 16 hours. After cooling to room temperature, the mixture was quenched with saturated aqueous NH4Cl (20 mL), extracted with EtOAc (20 mL×3). The combined organic layers were washed with H2O (20 mL) and brine (20 mL), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column (PE/EtOAc=300/1 to 200/1) to give the product (210 mg, yield 85%) as a solid.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. customthe mixture was quenched with saturated aqueous NH4Cl (20 mL)
  3. extractionextracted with EtOAc (20 mL×3)
  4. washThe combined organic layers were washed with H2O (20 mL) and brine (20 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give the crude product
  9. customThe crude product was purified by silica gel column (PE/EtOAc=300/1 to 200/1)

Quellen und Nachweise

ORD-Eintrag
ord-b88c74d2a79246f7acf9fe564c887fdb
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09249132B2

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