Ammonium Chloride → HCID 66667330, Verbindung

HRID 1618025

Reaktionsgleichung

Reaktionsgleichung von HRID 1618025
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1I.[Cl-].[Li+].C([Mg]Cl)(C)C.[CH2:17]([O:19][C:20](=[O:32])[C:21]([C:30]#[N:31])=[CH:22][C:23]1[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][CH:24]=1)[CH3:18].[Cl-].[NH4+]>C1COCC1>[CH2:17]([O:19][C:20](=[O:32])[CH:21]([C:30]#[N:31])[CH:22]([C:23]1[CH:24]=[CH:25][C:26]([Br:29])=[CH:27][CH:28]=1)[C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[F:1])[CH3:18]

Komponenten

6

Edukt 4

HCID 25517Ammonium ChlorideHCID 1375192,4-Difluoro-1-iodobenzeneHCID 367501Ethyl 3-(4-bromophenyl)-2-cyanoprop-2-enoateHCID 178461733HCID 178461733, Verbindung

Produkt 1

HCID 66667330HCID 66667330, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 2,4-difluoro-1-iodo-benzene (12.0 g) in anhydrous THF (200 mL) was added a solution of isopropylmagnesium chloride lithium chloride complex (52.9 mL, 14% solution in THF) slowly over 10 min at room temperature. After stirring for 1 h, a solution of 3-(4-bromo-phenyl)-2-cyano-acrylic acid ethyl ester (10.0 g; example 74, step 1) in anhydrous THF (100 mL) was added and stirring continued at room temperature. After 1 h, a saturated aq. solution of ammonium chloride was added (100 mL), the phases separated and the aqueous layer extracted with ethyl acetate (3×100 mL). The combined organic phases were dried over sodium sulfate and the crude reaction product purified by silica gel chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane/ethyl acetate (1:0 to 3:1) to provide the title compound as a light yellow oil. MS (ESI−): m/z=391.9 ([M−H]−).

Aufarbeitung

  1. stirringstirring
  2. customcontinued at room temperature
  3. waitAfter 1 h
  4. customthe phases separated
  5. extractionthe aqueous layer extracted with ethyl acetate (3×100 mL)
  6. dry with materialThe combined organic phases were dried over sodium sulfate
  7. customthe crude reaction product
  8. custompurified by silica gel chromatography
  9. washeluting with a gradient of n-heptane/ethyl acetate (1:0 to 3:1)

Quellen und Nachweise

ORD-Eintrag
ord-2a1c076de48d4bdb84e293a8622722f7
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765730B2

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