Methyl iodide → 1-(4-bromophenyl)ethyl methyl ether

HRID 220557

Reaktionsgleichung

Reaktionsgleichung von HRID 220557
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:10])[CH3:9])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:13]I>CN(C)C=O>[CH3:2][CH2:3][CH2:4][CH:5]([CH3:8])[CH3:6].[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:10][CH3:13])[CH3:9])=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 953521-(4-Bromophenyl)ethanol

Produkt 2

HCID 78922-MethylpentaneHCID 109658901-(4-bromophenyl)ethyl methyl etherAusbeute 195,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Dissolve 1-(4-bromo-phenyl)-ethanol (0.79 mL, 6.62 mmol) in dry N,N-dimethylformamide (7 mL) at ambient temperature under nitrogen atmosphere. Add sodium hydride (60% dispersion in oil, 397 mg, 9.93 mmol), stir the reaction for 30 min., then add methyl iodide (0.50 mL, 7.94 mmol) and stir the reaction for a further 23 hr. under nitrogen. Quench with water (30 mL), extract with DCM (3×30 mL), pass through an IST Phase Separator Frit® and concentrate. Purify using silica gel chromatography, eluting with 0:100 to 20:80 ethyl acetate: isohexane to give 1-bromo-4-(1-methoxy-ethyl)-benzene as a clear oil (1.39 g, 98%). 1H-NMR (400 MHz, CDCl3) δ 7.47 (d, 2H), 7.20 (d, 2H), 4.25 (q, 1H), 3.21 (s, 3H), 1.40 (d, 3H).

Aufarbeitung

  1. customthe reaction for 30 min.
  2. customthe reaction for a further 23 hr
  3. customQuench with water (30 mL)
  4. extractionextract with DCM (3×30 mL)
  5. concentrationconcentrate
  6. customPurify
  7. washeluting with 0:100 to 20:80 ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-5f48e7b3fa16492d89c49e40f7742909
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202873B2

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