N-bromobutanimide → ethyl 5-bromo-1,4-dimethyl-1H-pyrrole-2-carboxylate

HRID 1508497Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1508497
[CH3:1][N:2]1[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[Br:13]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:13][C:6]1[N:2]([CH3:1])[C:3]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:4][C:5]=1[CH3:7]

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 14296950ethyl 1,4-dimethyl-1H-pyrrole-2-carboxylate

Produkt 1

HCID 67516409ethyl 5-bromo-1,4-dimethyl-1H-pyrrole-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of ethyl 1,4-dimethyl-1H-pyrrole-2-carboxylate (63 mg, 0.377 mmol) in CHCl3 (3.5 mL) at 0° C. was added N-bromosuccinimide (67.1 mg, 0.377 mmol). The reaction was stirred at 0° C. for 15 min. The reaction was warmed to room temperature and stirred overnight. The reaction mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by preparative TLC (1000 μm, hexanes/EtOAc (9:1)) to give ethyl 5-bromo-1,4-dimethyl-1H-pyrrole-2-carboxylate. LCMS calc.=245.0. found=245.9 (M+H)+. 1H NMR (500 MHz, CDCl3): δ 6.83 (s, 1H); 4.27 (q, J=7.1 Hz, 2H); 3.91 (s, 3H); 2.05-2.02 (m, 3H); 1.34 (t, J=7.1 Hz, 3H).

Aufarbeitung

  1. temperatureThe reaction was warmed to room temperature
  2. stirringstirred overnight
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was purified by preparative TLC (1000 μm, hexanes/EtOAc (9:1))

Quellen und Nachweise

ORD-Eintrag
ord-7fb169b1beb84f2d9e71975dec1c2979
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09221834B2

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