Methyl iodide → 1-(4-Bromo-2-fluorophenyl)ethanol

HRID 1404773Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1404773
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([F:10])[CH:3]=1.[CH3:11][Mg]I.[Mg].CI>C(OCC)C>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([OH:7])[CH3:11])=[C:4]([F:10])[CH:3]=1

Komponenten

6

Edukt 4

HCID 6328Methyl iodideHCID 1435174-Bromo-2-fluorobenzaldehydeHCID 5462224MagnesiumHCID 178418373HCID 178418373, Verbindung

Produkt 1

HCID 596944341-(4-Bromo-2-fluorophenyl)ethanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

A solution of 4-bromo-2-fluorobenzaldehyde (5 g, 24.62 mmol) in diethyl ether (10 ml) was added to an ice-cold solution of methylmagnesium iodide prepared from magnesium (1.7 g, 73.88 mmol) and methyliodide (4.58 ml, 73.88 mmol) in diethyl ether (50 ml). The mixture was warmed stirred at RT, for 12 h, and cooled to 0° C., quenched with dil. 6N HCl and extracted with ethyl acetate. The organic layer was dried over sodium sulphate and concentrated under reduced pressure to afford the title compound as red colour liquid (5 g, 94%), 1H-NMR (δ ppm, CDCl3, 400 MHz): δ7.40 (t, J=8.2 Hz, 1H), 7.30 (dd, J=8.3. 1.7 Hz, 1H), 7.21 (dd, J=9.9, 1.9 Hz, 1H), 5.17 (q, J=6.4 Hz, 1H), 1.49 (d, J=6.5 Hz, 3H).

Aufarbeitung

  1. temperatureThe mixture was warmed
  2. temperaturecooled to 0° C.
  3. customquenched with dil. 6N HCl
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over sodium sulphate
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5ad0f40b00f54477b23c31c99c35f55c
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08912331B2

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