4-Fluorophenol → Methyl 4-[(4E)-3-(4-cyanobenzyl)-5-{2-[4-(4-fluorophenoxy)butoxy]phenyl}pent-4-en-1-yl]benzoate

HRID 1913799Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1913799
Br[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1/[CH:13]=[CH:14]/[CH:15]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]#[N:36])=[CH:31][CH:30]=1)[CH2:16][CH2:17][C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=1.[F:37][C:38]1[CH:43]=[CH:42][C:41]([OH:44])=[CH:40][CH:39]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:35]([C:32]1[CH:33]=[CH:34][C:29]([CH2:28][CH:15](/[CH:14]=[CH:13]/[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][CH2:5][CH2:4][CH2:3][CH2:2][O:44][C:41]2[CH:42]=[CH:43][C:38]([F:37])=[CH:39][CH:40]=2)[CH2:16][CH2:17][C:18]2[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=2)=[CH:30][CH:31]=1)#[N:36]

Komponenten

5

Edukt 3

HCID 97324-FluorophenolHCID 11430Potassium CarbonateHCID 59180489Methyl 4-[(4E)-5-[2-(4-bromobutoxy)phenyl]-3-(4-cyanobenzyl)pent-4-en-1-yl]benzoate

Produkt 1

HCID 59180544Methyl 4-[(4E)-3-(4-cyanobenzyl)-5-{2-[4-(4-fluorophenoxy)butoxy]phenyl}pent-4-en-1-yl]benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of 392 mg (0.72 mmol) of methyl 4-[(4E)-5-[2-(4-bromobutoxy)phenyl]-3-(4-cyanobenzyl)pent-4-en-1-yl]benzoate in 10 ml of dry acetonitrile is mixed with 120 mg (1.08 mmol) of 4-fluorophenol and 148 mg (1.08 mmol) of anhydrous potassium carbonate and then heated under reflux for 12 h. The mixture is subsequently filtered, and the filtrate is evaporated to dryness. 445 mg (0.71 mmol, purity 93%, 99% of theory) of a yellowish oil are isolated.

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux for 12 h
  3. filtrationThe mixture is subsequently filtered
  4. customthe filtrate is evaporated to dryness
  5. custom445 mg (0.71 mmol, purity 93%, 99% of theory) of a yellowish oil are isolated

Quellen und Nachweise

ORD-Eintrag
ord-c6cfb97521d044008c8c9efb3dc01588
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08609727B2

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