1,2-Dichloroethane → (4-Bromo-3-fluorophenyl)(morpholin-4-yl)methanone

HRID 882965

Reaktionsgleichung

Reaktionsgleichung von HRID 882965
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[F:11].[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.C(N1CCOCC1)C.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[O:8])=[CH:4][C:3]=1[F:11]

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 7525EthylmorpholineHCID 8083MorpholineHCID 757711-HydroxybenzotriazoleHCID 27733414-Bromo-3-fluorobenzoic acid

Produkt 1

HCID 48474115(4-Bromo-3-fluorophenyl)(morpholin-4-yl)methanoneAusbeute 98,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A 500 mL flask was charged with 4-bromo-3-fluorobenzoic acid (5.00 g, 22.83 mmol), 100 mL DMF, morpholine (2.4 ml, 27.5 mmol), and 4-Ethylmorpholine (8.6 ml, 67.9 mmol). HOBt (4.32 g, 32.0 mmol) was added followed by EDC (5.25 g, 27.4 mmol) and the reaction allowed to stir at room temperature for 18 hours. The reaction was concentrated and the resulting orange syrup taken up in 100 mL EtOAc and 100 mL water. The organic layer was washed with 100 mL 2N HCl, 100 mL saturated sodium bicarbonate, and 100 mL saturated sodium chloride. The organic was then dried with MgSO4, filtered, and concentrated to give 6.476 g (98%) of a viscous yellow oil. This material was used without further purification.

Aufarbeitung

  1. concentrationThe reaction was concentrated
  2. washThe organic layer was washed with 100 mL 2N HCl, 100 mL saturated sodium bicarbonate, and 100 mL saturated sodium chloride
  3. dry with materialThe organic was then dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-77d51c2daee940da81507bf578f69cff
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08236799B2

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