Benzyl Bromide → HCID 68753687, Verbindung

HRID 333322

Reaktionsgleichung

Reaktionsgleichung von HRID 333322
[C:1]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][C:9]([OH:11])=[O:10])=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].[CH:24]1[CH:29]=[CH:28][C:27]([CH2:30]Br)=[CH:26][CH:25]=1>CN(C=O)C.O>[C:1]1([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][C:9]([O:11][CH2:30][C:27]2[CH:28]=[CH:29][CH:24]=[CH:25][CH:26]=2)=[O:10])=[CH:3][CH:2]=1

Komponenten

6

Edukt 3

HCID 7498Benzyl Bromide2×HCID 11430Potassium CarbonateHCID 30824342(4-Biphenyl)propionic acid

Produkt 1

HCID 68753687HCID 68753687, VerbindungAusbeute 88,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a suspension of 3-(biphenyl-4-yl)propanoic acid (5 g, 22.10 mmol) and K2CO3 (6.11 g, 44.2 mmol) in DMF (22 ml), BnBr (3.94 ml, 33.1 mmol) was added. After stirred for 15 hours, additional BnBr (3.94 ml, 33.1 mmol) was added. After stirred for further 22 hours, the reaction was diluted with H2O, extracted with EtOAc, washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The obtained residue was diluted with EtOAc (150 ml), and NH-silica gel was added to the suspension. The EtOAc was evaporated, and the resulted slurry was allowed to stir for 1 hour. The slurry was eluted with 10% EtOAc/heptane (150 ml) to give benzyl 3-(biphenyl-4-yl)propanoate (6.16 g); Retention time=1.71 minutes (condition A); 1H NMR (400 MHz, CDCl3) δ ppm 2.72 (t, J=7.8 Hz, 2H) 3.01 (t, J=7.8 Hz, 2H) 5.12 (s, 2H) 7.21-7.47 (m, 14H).

Aufarbeitung

  1. additionwas added
  2. stirringAfter stirred for further 22 hours
  3. extractionextracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. additionThe obtained residue was diluted with EtOAc (150 ml), and NH-silica gel
  9. additionwas added to the suspension
  10. customThe EtOAc was evaporated
  11. stirringto stir for 1 hour
  12. washThe slurry was eluted with 10% EtOAc/heptane (150 ml)

Quellen und Nachweise

ORD-Eintrag
ord-b78513581fb14ee78dd3ce13c4628a39
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877815B2

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