Ethyl 4-bromobenzoate → Ethyl 4-(4-n-pentyloxyphenylethynyl)benzoate

HRID 351536

Reaktionsgleichung

Reaktionsgleichung von HRID 351536
Br[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[CH2:13]([O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]#[CH:26])=[CH:21][CH:20]=1)[CH2:14][CH2:15][CH2:16][CH3:17]>C(N(CC)CC)C.N1C=CC=CC=1.[Cu]I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:13]([O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]#[C:26][C:2]2[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=2)=[CH:21][CH:20]=1)[CH2:14][CH2:15][CH2:16][CH3:17]

Komponenten

8

Edukt 2

HCID 22043Ethyl 4-bromobenzoateHCID 27751191-Eth-1-ynyl-4-(pentyloxy)benzene

Produkt 1

HCID 22713259Ethyl 4-(4-n-pentyloxyphenylethynyl)benzoateAusbeute 35,2 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 11776TriphenylphosphineKatalysatorHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6102075Dichlorobis(triphenylphosphine)palladiumKatalysatorHCID 1049PyridineLösungsmittelHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a suspension of ethyl 4-bromobenzoate (1.37 g), (4-n-pentyloxyphenyl)acetylene (565 mg), triphenylphosphine (16 mg) and copper(I) iodide (6 mg) in triethylamine (10 ml) and pyridine (4 ml) was added palladium(II) chloride bis(triphenylphosphine) (21 mg) and the reaction mixture was stirred for 24 hours at 80° C. After cooling, the precipitate was filtered off, and the filtrate was evaporated under reduced pressure. The residue was taken up to dichloromethane, and the solution was washed successively with 1N HCl, water, brine and dried over magnesium sulfate. The solvents were removed under reduced pressure and the residue was triturated with acetonitrile, collected by filtration and dried under reduced pressure to give ethyl 4-(4-n-pentyloxyphenylethynyl)benzoate (355 mg).

Aufarbeitung

  1. temperatureAfter cooling
  2. filtrationthe precipitate was filtered off
  3. customthe filtrate was evaporated under reduced pressure
  4. washthe solution was washed successively with 1N HCl, water, brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvents were removed under reduced pressure
  7. customthe residue was triturated with acetonitrile
  8. filtrationcollected by filtration
  9. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-75df36affa3b4e1c9e154e2606ab4cdf
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06743776B2

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