Carbon tetrabromide → 4-(Bromomethyl)-1-(4-fluorophenyl)pyrrolidin-2-one

HRID 855578Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 855578
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH:11]([CH2:13]O)[CH2:10][C:9]2=[O:15])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:36]>N1C=CC=CC=1>[Br:36][CH2:13][CH:11]1[CH2:12][N:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[C:9](=[O:15])[CH2:10]1

Komponenten

5

Edukt 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 104656771-(4-Fluorophenyl)-4-(hydroxymethyl)pyrrolidin-2-one

Produkt 1

HCID 219354874-(Bromomethyl)-1-(4-fluorophenyl)pyrrolidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a cooled solution of 1-(4-fluorophenyl)-4-(hydroxymethyl)pyrrolidin-2-one (0.05 g, 0.25 mmol) in pyridine (3 ml) was added triphenylphosphine (0.130 g, 0.5 mmol). The solution was stirred and carbon tetrabromide (0.08 g, 0.25 mmol) was added in 3 separate portions. The reaction mixture was then allowed to warm to room temperature and stirred for three hours. The reaction was quenched with methanol and the solvent removed. The residue was dissolved in EtOAc (75 ml) and sequentially washed with ammonium chloride (sat, 2×25 ml) and water (25 ml). The organic layer was concentrated and purified using preparative tlc (1:1 EtOac:Hexanes) to yield 4-(bromomethyl)-1-(4-fluorophenyl)pyrrolidin-2-one (HNMR).

Aufarbeitung

  1. customseparate portions
  2. stirringstirred for three hours
  3. customThe reaction was quenched with methanol
  4. customthe solvent removed
  5. dissolutionThe residue was dissolved in EtOAc (75 ml)
  6. washsequentially washed with ammonium chloride (sat, 2×25 ml) and water (25 ml)
  7. concentrationThe organic layer was concentrated
  8. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-94316ccb9c33428b83a391269b59e010
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07262198B2

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