4-(Bromoacetyl)benzonitrile → 4-(2-Hydroxyacetyl)benzonitrile

HRID 572583Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 572583
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[N:12])=[CH:7][CH:6]=1)=[O:4].C([O-])=[O:14].[Na+]>CO>[OH:14][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[N:12])=[CH:7][CH:6]=1)=[O:4]

Komponenten

4

Edukt 2

HCID 986544-(Bromoacetyl)benzonitrileHCID 2723810Sodium Formate

Produkt 1

HCID 179928864-(2-Hydroxyacetyl)benzonitrileAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 2-Bromo-1-(4-cyanophenyl)ethanone (15 g, 0.067 mol) in methanol (200 ml) was added sodium formate (13.6 g, 0.201 mol) at RT. The reaction mixture was refluxed for 15 h and filtered. The filtrate was concentrated under reduced pressure. The residue was dissolved with ethyl acetate, washed with water and brine solution, dried over Na2SO4 and evaporated. The crude material was purified by column chromatography using petroleum ether and ethyl acetate (60:40) as an eluent to afford (5.4 g, 50%) of title compound as an off white solid. 1H NMR: (DMSO-d6, 400 MHz) δ 8.06-8.04 (dd, J=1.9, 6.7 Hz, 2H), 8.00-7.98 (dd, J=1.9, 6.7 Hz, 2H), 5.27-5.24 (t, J=5.9 Hz, 1H), 4.82-4.80 (d, J=5.9 Hz, 2H).

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 15 h
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. dissolutionThe residue was dissolved with ethyl acetate
  5. washwashed with water and brine solution
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. customThe crude material was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-514d75b9894e41878c9d71b65bb7679f
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029405B2

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