Sodium Iodide → 2-Iodo-3',4',5'-tribenzyloxyacetophenone

HRID 1894919Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1894919
Br[CH2:2][C:3]([C:5]1[CH:10]=[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:8]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:7]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:6]=1)=[O:4].[I-:35].[Na+]>C(#N)C>[I:35][CH2:2][C:3]([C:5]1[CH:10]=[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:8]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:7]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:6]=1)=[O:4]

Komponenten

4

Edukt 2

HCID 5238Sodium IodideHCID 576727852-Bromo-3',4',5'-tribenzyloxyacetophenone

Produkt 1

HCID 576727822-Iodo-3',4',5'-tribenzyloxyacetophenone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

2-Bromo-3′,4′,5′-tribenzyloxyacetophenone (5.17 g, 10.0 mmol) (11) and sodium iodide (2.25 g, 15 mmol) were dissolved in dry acetonitrile (50 mL) and stirred at room temperature overnight. The solution was filtered and acetonitrile removed under vacuum. Water (30 mL) was added and the solution was extracted with diethyl ether (4×25 mL). The organic phase was dried (MgSO4) and the solvents removed in vacuo. Recrystallisation from methylcyclohexane afforded the titled compound as yellow crystals, m.p. 110-112° C. Yield 3.6 g (64%). 1H NMR (300 MHz, CDCl3): δ=4.21 (2H, s), 5.15 (6H, s), 7.22-7.48 (17H, m); 13C NMR (75 MHz): δ=1.0, 71.3, 75.1, 109.0, 127.4, 127.9, 128.0, 128.1, 128.3, 128.4, 128.5, 136.3, 137.1, 143.4, 152.6, 191.5.

Aufarbeitung

  1. filtrationThe solution was filtered
  2. customacetonitrile removed under vacuum
  3. additionWater (30 mL) was added
  4. extractionthe solution was extracted with diethyl ether (4×25 mL)
  5. dry with materialThe organic phase was dried (MgSO4)
  6. customthe solvents removed in vacuo
  7. customRecrystallisation from methylcyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-5c7db2ee15b54cb1ae1caf06d1e7e641
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08513395B2

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