Methyl iodide → 1-Bromo-3-(methoxymethyl)-5-nitrobenzene

HRID 410403

Reaktionsgleichung

Reaktionsgleichung von HRID 410403
[Br:1][C:2]1[CH:3]=[C:4]([CH2:11][OH:12])[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.I[CH3:14].[H-].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([CH2:11][O:12][CH3:14])[CH:3]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 14866972(3-Bromo-5-nitrophenyl)methanol

Produkt 1

HCID 672485781-Bromo-3-(methoxymethyl)-5-nitrobenzeneAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of (3-bromo-5-nitrophenyl)methanol (500 mg, 2.155 mmol) in DMF (7.2 mL) was added iodomethane (0.40 mL, 6.46 mmol. The solution was cooled to 0° C. before NaH (60% dispersion in mineral oil, 172 mg, 4.31 mmol) was added. The reaction was stirred at 0° C. and allowed to come to room temperature. After 2 hours the reaction was quenched with water and ethyl acetate was then added. Extraction was done with ethyl acetate (3×). The combined organic layer was dried over magnesium sulfate and then filtered. Ethyl acetate was then removed in vacuo to afford 1-bromo-3-(methoxymethyl)-5-nitrobenzene (470 mg, 1.910 mmol, 89% yield) as a yellow solid. 1H NMR (500 MHz, DMSO-d6) δ 8.25 (s, 1H), 8.13 (s, 1H), 7.96 (s, 1H), 4.53 (s, 2H), 3.33 (s, 3H).

Aufarbeitung

  1. additionwas added
  2. customto come to room temperature
  3. customAfter 2 hours the reaction was quenched with water and ethyl acetate
  4. additionwas then added
  5. extractionExtraction
  6. dry with materialThe combined organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. customEthyl acetate was then removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-73b038df3e394e14adf20762efe2023a
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759366B2

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