Bromine → 3-bromo-2-phenyl-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole

HRID 2252036

Reaktionsgleichung

Reaktionsgleichung von HRID 2252036
[C:1]1([C:7]2[N:8]=[C:9]3[CH2:14][CH2:13][CH2:12][N:10]3[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:15]Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:15][C:11]1[N:10]2[CH2:12][CH2:13][CH2:14][C:9]2=[N:8][C:7]=1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

5

Edukt 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 7655112-Phenyl-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole

Produkt 1

HCID 40792973-bromo-2-phenyl-6,7-dihydro-5H-pyrrolo[1,2-a]imidazoleAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-phenyl-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole (3.38 g, 18.3 mmol) in dry CH2Cl2 (113 mL) slowly add bromine (1.0 mL, 20.2 mmol) and stir the mixture at room temperature for 1.5 hours. Add a saturated aqueous solution of NaHCO3 (100 mL) and extract with CH2Cl2 (3×100 mL). Wash the combined organic layers with NaHSO3 (40%, 30 mL), dry (MgSO4) and concentrate in vacuo. Purify the residue by flash chromatography (SiO2, eluent: CH2Cl2 to CH2Cl2/MeOH 20:1) to yield a red solid, 3.54 g, 73% yield. MS(ES+): m/z=263.0 (M+H)+

Aufarbeitung

  1. extractionextract with CH2Cl2 (3×100 mL)
  2. washWash the combined organic layers with NaHSO3 (40%, 30 mL)
  3. dry with materialdry (MgSO4)
  4. concentrationconcentrate in vacuo
  5. customPurify the residue by flash chromatography (SiO2, eluent: CH2Cl2 to CH2Cl2/MeOH 20:1)
  6. customto yield a red solid, 3.54 g, 73% yield

Quellen und Nachweise

ORD-Eintrag
ord-c2e4c316178d433fa63965910280354b
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07320995B2

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