Hydrochloric Acid → HCID 57701129, Verbindung

HRID 332574

Reaktionsgleichung

Reaktionsgleichung von HRID 332574
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6].I[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=1.C([O-])([O-])=O.[Cs+].[Cs+].CN(C)CC(O)=O.Cl>O1CCOCC1.[Cu]I>[Cl:19][C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=1)[O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6]

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 673N,N-DimethylglycineHCID 10796Cesium carbonateHCID 12127IsovanillinHCID 122691-Chloro-3-iodobenzene

Produkt 1

HCID 57701129HCID 57701129, VerbindungAusbeute 24 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
98 °C

Versuchsvorschrift

To a 250 mL pressure resistant vial which contained a mixture of 3-hydroxy-4-methoxy-benzaldehyde (1520 mg, 10 mmole), 1-Iodo-3-chloro-benzene (2390 mg, 10 mmole), Cs2CO3 (1600 mg, 10 mmole) and N,N-dimethylglycine.HCl (280 mg, 2 mmole) in dioxane (40 mL) was added CuI (380 mg, 2 mmole) at rt. The reaction mixture was bumbled with Ar for 5 min at rt and then the vial was sealed. The reaction mixture was heated to 98° C. and stirred for 24 h and then 110° C. for 20 h. After cooling to rt, the reaction mixture was poured onto 250 mL ice-water which was extracted with ethyl acetate (3×50 mL), washed with water (2×50 mL), brine (50 mL) and dried over Na2SO4. After removal of solvent, the residue was purified by silica gel column chromatography with ethyl acetate/hexane as eluent to give 500 mg (24% yield) of product (12).

Aufarbeitung

  1. customthe vial was sealed
  2. wait110° C. for 20 h
  3. temperatureAfter cooling to rt
  4. extractionwas extracted with ethyl acetate (3×50 mL)
  5. washwashed with water (2×50 mL), brine (50 mL)
  6. dry with materialdried over Na2SO4
  7. customAfter removal of solvent
  8. customthe residue was purified by silica gel column chromatography with ethyl acetate/hexane as eluent

Quellen und Nachweise

ORD-Eintrag
ord-70adf1ee74c240c09febc757ea2010ea
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877816B2

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