Pyrrolidine → 1-(2-Bromo-3-methylbenzoyl)pyrrolidine

HRID 1028935

Reaktionsgleichung

Reaktionsgleichung von HRID 1028935
[Br:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1>C1COCC1>[Br:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([N:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:6]

Komponenten

4

Edukt 2

HCID 31268PyrrolidineHCID 27355882-Bromo-3-methylbenzoic acid

Produkt 1

HCID 665791491-(2-Bromo-3-methylbenzoyl)pyrrolidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2-Bromo-3-methylbenzoic acid (5.0 g, 23.3 mmol) was dissolved in THF (100 mL) and added N,N′-carbonyldiimidazole (4.52 g, 27.9 mmol). The reaction mixture was stirred at ambient temperature for 14 h. Pyrrolidine (6.8 mL, 81 mmol) was added in one portion. The mixture was stirred for 8 h and then partitioned between EtOAc and water. The organic layer was washed with water, diluted HCl, saturated bicarbonate, water and brine. The solution was then concentrated in vacuo to afford (2-bromo-3-methylphenyl)(pyrrolidin-1-yl)methanone as a white crystalline solid, upon standing overnight at RT.

Aufarbeitung

  1. stirringThe mixture was stirred for 8 h
  2. custompartitioned between EtOAc and water
  3. washThe organic layer was washed with water, diluted HCl, saturated bicarbonate, water and brine
  4. concentrationThe solution was then concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a11937687535417686898b6081575465
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08735384B2

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