Water → 1-(3-Chloro-2-hydroxy-4-((4-iodobenzyl)oxy)phenyl)ethanone

HRID 1818553Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1818553
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([I:9])=[CH:5][CH:4]=1.[Cl:10][C:11]1[C:12]([OH:21])=[C:13]([C:18](=[O:20])[CH3:19])[CH:14]=[CH:15][C:16]=1[OH:17].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[Cl:10][C:11]1[C:12]([OH:21])=[C:13]([C:18](=[O:20])[CH3:19])[CH:14]=[CH:15][C:16]=1[O:17][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([I:9])=[CH:5][CH:4]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 10796Cesium carbonateHCID 9542584-Iodobenzyl bromideHCID 574382941-(3-Chloro-2,4-dihydroxy-phenyl)ethanone

Produkt 1

HCID 574383881-(3-Chloro-2-hydroxy-4-((4-iodobenzyl)oxy)phenyl)ethanoneAusbeute 29,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Add 1-bromomethyl-4-iodo-benzene (10.00 g, 33.7 mmol) to a solution of 1-(3-chloro-2,4-dihydroxy-phenyl)-ethanone (7.92 g, 42.4 mmol) and cesium carbonate (16.6 g, 50.9 mmol) in dimethylformamide (250 mL) and stir. After 18 hours, pour reaction into water and extract with ethyl acetate. Combine organic layers and wash with 2N NaOH. Dry with sodium sulfate, filter, and concentrate under reduced pressure to give a residue. Purify the residue by flash chromatography eluting with a gradient of ethyl acetate:hexanes to yield the title product as a tan solid (4.00 g, 23%): 1H NMR (DMSO-d6) δ 2.62 (s, 3H), 5.33 (s, 2H), 6.87 (d, 1H), 7.27 (d, 2H), 7.78 (d, 2H), 7.94 (d, 1H), 13.13 (s, 1H).

Aufarbeitung

  1. additionpour
  2. extractionextract with ethyl acetate
  3. washCombine organic layers and wash with 2N NaOH
  4. dry with materialDry with sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate under reduced pressure
  7. customto give a residue
  8. customPurify the residue by flash chromatography
  9. washeluting with a gradient of ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-8d61fe2b32094a679fe550a43316d6a1
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07598423B2

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