Ammonium Chloride → 1-(4-Ethyl-4-penten-1-yl)-2-iodobenzene

HRID 600745Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 600745
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[I:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][CH2:14][CH2:15]C(=O)CC.[Cl-].[NH4+]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCOCC>[CH2:2]([C:3](=[CH2:4])[CH2:15][CH2:14][CH2:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[I:6])[CH3:1]

Komponenten

6

Edukt 3

HCID 25517Ammonium ChlorideHCID 116236086-(2-Iodophenyl)-3-hexanone2×HCID 178418339Butyllithium

Produkt 1

HCID 116379981-(4-Ethyl-4-penten-1-yl)-2-iodobenzeneAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74505Methyltriphenyliphosphonium bromideKatalysatorHCID 3283Diethyl EtherLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A suspension of methyltriphenylphosphonium bromide (21.76 g, 61 mmol) in dry ether (300 ml) was stirred at 0° C. under nitrogen. To this was added a 1.6M solution of butyl lithium (33.3 ml, 53.3 mmole) dropwise. Stirring at 0° C. was continued for 45 min then a solution of 6-(2-iodophenyl)-3-hexanone (Intermediate 10) (11.5 g, 38 mmol) in dry ether (40 ml) was added dropwise. Stirring at 0° C. was continued for 3 hours after which time aqueous ammonium chloride solution was added and the mixture was extracted with ether. The combined extracts were washed once with a mixture of ammonium chloride and sodium chloride solutions, dried over anhydrous magnesium sulphate and evaporated in vacuo. The residue was slurried with cyclohexane to extract the crude product. Purification by SPE eluting with cyclohexane gave the title compound as a colourless liquid (6.8 g, 60%).

Aufarbeitung

  1. stirringStirring at 0° C.
  2. stirringStirring at 0° C.
  3. waitwas continued for 3 hours
  4. extractionthe mixture was extracted with ether
  5. washThe combined extracts were washed once with a mixture of ammonium chloride and sodium chloride solutions
  6. dry with materialdried over anhydrous magnesium sulphate
  7. customevaporated in vacuo
  8. extractionto extract the crude product
  9. customPurification by SPE
  10. washeluting with cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-0a4dcf269c9847688354bf6dea376217
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902224B2

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