Morpholine → 4-(2-Fluoro-4-iodobenzyl)morpholine

HRID 56072Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 56072
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[CH3:9].C1C(=O)N(Br)C(=O)C1.[NH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1>C(Cl)(Cl)Cl.CCO>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[CH2:9][N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1

Komponenten

6

Edukt 3

HCID 8083MorpholineHCID 67184N-bromobutanimideHCID 1234922-Fluoro-4-iodotoluene

Produkt 1

HCID 900233414-(2-Fluoro-4-iodobenzyl)morpholineAusbeute 15 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a solution of 2-fluoro-4-iodotoluene (23.60 g, 0.10 mol) in CHCl3 (1000 mL) was added BPO (0.55 g, 2.27 mmol) and NBS (24.92 g, 0.14 mol) under N2. The reaction mixture was refluxed for 6 h, then cooled and filtered. The filtrate was concentrated in vacuo. The residue was added to a solution of morpholine (43.56 g, 0.50 mol) in EtOH (1000 mL) under N2. The resulting mixture was stirred at rt overnight, and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=3:1) to give the title compound as a white solid (4.82 g, 15%).

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 6 h
  2. temperaturecooled
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=3:1)

Quellen und Nachweise

ORD-Eintrag
ord-2e533e89b32a4745b6d0db5d1eb08b3a
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434695B2

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