Sodium Bicarbonate → 4-Iodo-2-nitrobenzaldehyde

HRID 456316Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 456316
[C:1]([O-:4])(O)=O.[Na+].BrC[C:8]1[CH:13]=[CH:12][C:11]([I:14])=[CH:10][C:9]=1[N+:15]([O-:17])=[O:16]>CS(C)=O.O>[I:14][C:11]1[CH:12]=[CH:13][C:8]([CH:1]=[O:4])=[C:9]([N+:15]([O-:17])=[O:16])[CH:10]=1

Komponenten

5

Edukt 2

HCID 516892Sodium BicarbonateHCID 179660241-(Bromomethyl)-4-iodo-2-nitrobenzene

Produkt 1

HCID 215327854-Iodo-2-nitrobenzaldehydeAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
86 °C

Versuchsvorschrift

NaHCO3 (3.32 g, 39.48 mmol) was added to a solution of 1-bromomethyl-4-iodo-2-nitrobenzene (2.25 g, 6.58 mmol) in anhydrous DMSO (150 mL). The mixture was stirred at 86° C. for 19 hours under a nitrogen atmosphere, then cooled down to room temperature, diluted with water (300 mL), and extracted with methylene chloride four times (250 mL). The combined organic phase was dried over Na2SO4, concentrated in vacuo, and purified by silica gel chromatography to yield 4-iodo-2-nitrobenzaldehyde (1.11 g, 61%). 1HNMR (400 MHz, CDCl3): δ 10.38 (d, 1 H, J=1.6 Hz, CHO), 8.45 (d, 1 H, J=1.5 Hz, Ph-H), 8.15 (dd, 1 H, J=1.5 and 8.0 Hz, Ph-H), 7.67 (d, 1 H, J=8.1 Hz, Ph-H); 13C NMR (100 MHz, CDCl3): δ 187.28 (CH), 143.18 (CH), 133.29 (CH), 130.67 (CH), 130.28 (C), 109.60 (C), 99.78 (C).

Aufarbeitung

  1. temperaturecooled down to room temperature
  2. extractionextracted with methylene chloride four times (250 mL)
  3. dry with materialThe combined organic phase was dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. custompurified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-cf31a7c7c09949bb88fb4f87c6761234
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08497360B2

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