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

HRID 1161116Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1161116
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-cfc88861acda42f08105c6721c8c76f5
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07816523B2

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