1-Bromo-4-iodobenzene → 1-(4-Bromophenyl)pyrrolidine

HRID 1810182Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1810182
CC(C)([O-])C.[Na+].I[C:8]1[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][CH:9]=1.[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[Br:14][C:11]1[CH:12]=[CH:13][C:8]([N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:9][CH:10]=1

Komponenten

7

Edukt 3

HCID 115221-Bromo-4-iodobenzeneHCID 31268PyrrolidineHCID 23676156Sodium t-butoxide

Produkt 1

HCID 70164571-(4-Bromophenyl)pyrrolidineAusbeute 76,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 634876Binap, (A+-)-KatalysatorHCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A oven-dried 50 mL of round bottom flask is charged with Pd2(dba)3 (116 mg, 0.13 mmol), BINAP (158 mg, 0.25 mmol), and sodium tert-butoxide (916 mg, 9.54 mmol). The flask is evacuated and backfilled with argon. Degassed toluene (5 mL), 1-iodo-4-bromobenzene (1.8 g, 6.36 mmol), pyrrolidine (542 mg, 7.63 mmol) are then added. The mixture is heated at 80° C. until the starting aryl iodide is completed consumed judged by LC-MS analysis. The mixture is diluted with ethyl acetate, filtered through Celite, and concentrated in vacuo. The crude product is purified by flash chromatography to give 1.1 g of product as light brown solid. 1H NMR (400 MHz, CDCl3): δ 2.00 (t, 4H, J=4 Hz), 3.24 (t, 4H, J=4 Hz), 6.42 (d, 2H, J=8 Hz), 7.29 (d, 2H, J=8 Hz).

Aufarbeitung

  1. customThe flask is evacuated
  2. customis completed consumed
  3. additionThe mixture is diluted with ethyl acetate
  4. filtrationfiltered through Celite
  5. concentrationconcentrated in vacuo
  6. customThe crude product is purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7c4c93740c3f43bd840941cd20246053
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362063B2

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