Tetraethyltin → Methyl 5-chloro-2-ethylbenzoate

HRID 924674Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 924674
Br[C:2]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Cl-].[Li+].[CH2:15]([Sn](CC)(CC)CC)[CH3:16]>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[Cl:12][C:9]1[CH:10]=[CH:11][C:2]([CH2:15][CH3:16])=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5]

Komponenten

6

Edukt 3

HCID 11704TetraethyltinHCID 280500Methyl 2-Bromo-5-chlorobenzoateHCID 433294Lithium Chloride

Produkt 1

HCID 59382453Methyl 5-chloro-2-ethylbenzoateAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Methyl 2-bromo-5-chlorobenzoate (1.0 g, 4 mmol), lithium chloride (490 mg, 11.58 mmol), tetraethyltin (0.81 mL, 4.1 mmol) and bis(triphenylphosphine)-palladium(II)chloride (100 mg, 0.13 mmol) were combined in DMF (20 mL) and heated at 100° C. for 5 h. Solvent was removed at reduced pressure and the residue was diluted with water and EtOAc. The organic layer was separated, washed with water, dried over sodium sulfate and concentrated. Column chromatography on silica gel (0 to 10% EtOAc/hexane) provided the title compound (435 mg, 55%).

Aufarbeitung

  1. customSolvent was removed at reduced pressure
  2. additionthe residue was diluted with water and EtOAc
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-37111638b31e48d8be3ca34f6c7d5614
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09283224B2

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