Ethyl Bromide → Ethyl 4-cyanophenyl sulfide

HRID 2041172Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2041172
[SH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.Br[CH2:11][CH3:12].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:11]([S:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1)[CH3:12]

Komponenten

5

Edukt 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 5850584-Thiobenzonitrile

Produkt 1

HCID 21262891Ethyl 4-cyanophenyl sulfideAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Combine 4-mercapto-benzonitrile (0.4 g, 2.96 mmol), bromoethane (1.4 mL, 8.88 mmol) and potassium carbonate (3.3 g, 23.7 mmol) in anhydrous DMF (7 mL) and heat at 60° C. for 17 h. Cool the reaction mixture to ambient temperature and partition between brine (20 mL) and EtOAc (20 mL). Separate the organic layer, dry over anhydrous Na2SO4 and concentrate. Purify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 9:1 and 4:1) to obtain the desired intermediate as a colorless oil (0.4 g, 83%).

Aufarbeitung

  1. custompartition between brine (20 mL) and EtOAc (20 mL)
  2. customSeparate the organic layer
  3. dry with materialdry over anhydrous Na2SO4
  4. concentrationconcentrate
  5. customPurify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 9:1 and 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-cc74c0172f564d5a97ae26690dc8f0fd
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08580780B2

Notizen zur Reaktion

Wird geladen…