Azobisisobutyronitrile → 2-(4-Bromomethyl-thiophen-3-ylmethyl)-isoindole-1,3-dione

HRID 251251Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 251251
[CH3:1][CH:2]1[CH2:6][S:5][CH2:4][CH:3]1[CH2:7][N:8]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:18].C1C(=O)N([Br:26])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:26][CH2:1][C:2]1[C:3]([CH2:7][N:8]2[C:16](=[O:17])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:18])=[CH:4][S:5][CH:6]=1

Komponenten

5

Edukt 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 672731652-(4-Methyl-tetrahydro-thiophen-3-ylmethyl)-isoindole-1,3-dione

Produkt 1

HCID 672716532-(4-Bromomethyl-thiophen-3-ylmethyl)-isoindole-1,3-dioneAusbeute 53,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

2-(4-Methyl-tetrahydro-thiophen-3-ylmethyl)-isoindole-1,3-dione (410.0 mg, 1.59 mmol) and NBS (312.0 mg, 1.75 mmol) were dissolved in CCl4 (8.0 mL). AIBN (100 mg) was added in one portion. The mixture was heated at 85° C. under N2 for 90 min. After cooling down, the mixture was passed through a short silica gel column (4×10 cm), eluted with CH2Cl2. The solution obtained was concentrated and the residue was recrystallized from EtOAc/Hexanes (5/1) to give 2-(4-Bromomethyl-thiophen-3-ylmethyl)-isoindole-1,3-dione (285 mg, 50%) as a white solid. 1H NMR (CDCl3) δ 4.74 (s, 2H), 4.91 (s, 2H), 7.29-7.30 (d, 1H, J=3.3 Hz), 7.70-7.71 (d, 1H, J=3.3 Hz), 7.70-7.73 (m, 2H), 7.82-7.87 (m, 2H).

Aufarbeitung

  1. temperatureAfter cooling down
  2. washeluted with CH2Cl2
  3. customThe solution obtained
  4. concentrationwas concentrated
  5. customthe residue was recrystallized from EtOAc/Hexanes (5/1)

Quellen und Nachweise

ORD-Eintrag
ord-576e3dc1ea674f03bc26de2e591a35b7
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863293B2

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