Ammonium Chloride → 1-(5-Bromopyridin-2-yl)ethanol

HRID 1487502Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1487502
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]=[O:9])=[N:6][CH:7]=1.[CH3:10][Mg]Br.[Cl-].[NH4+]>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([OH:9])[CH3:10])=[N:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 98775625-Bromopyridine-2-carbaldehydeHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 426142881-(5-Bromopyridin-2-yl)ethanolAusbeute 73,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred solution of 5-Bromo-pyridine-2-carbaldehyde (10 g, 53.76 mmol) in tetrahydrofuran (200 mL) at 0° C. is added drop wise methyl magnesium bromide (45 mL, 64.51 mmol). Reaction mixture is stirred 0° C. for 6 hours and diluted using saturated ammonium chloride solution and extracted with ethyl acetate. Organic layer is dried over sodium sulphate, concentrated and purified by combiflash using 25% ethyl acetate in hexane as an eluent to give the title compound (8 g). 1H NMR (400 MHz, DMSO-d6) δ: 1.34 (d, J=6.52 Hz, 3H), 4.66-4.72 (m, 1H), 5.47 (d, J=4.76 Hz, 1H), 7.48 (d, 8.36 Hz, 1H), 8.021 (dd, J1=2.44 Hz, J2=8.44 Hz 1H), 8.58 (d, J=2.36 Hz, 1H). LC-Ms (m/z): 203.9 [M+H].

Aufarbeitung

  1. customReaction mixture
  2. additiondiluted
  3. extractionextracted with ethyl acetate
  4. dry with materialOrganic layer is dried over sodium sulphate
  5. concentrationconcentrated
  6. custompurified by combiflash

Quellen und Nachweise

ORD-Eintrag
ord-104e1c4a820640a5a697dddf525c00a3
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09428528B2

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