Methyl 4-(bromomethyl)benzoate → HCID 18510220, Verbindung

HRID 1371014

Reaktionsgleichung

Reaktionsgleichung von HRID 1371014
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:11][Si](C)(C)C)[C:9]#N)=[CH:4][CH:3]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.BrC[C:28]1[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][CH:29]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.O>[CH3:35][O:34][C:32](=[O:33])[C:31]1[CH:36]=[CH:37][C:28]([CH2:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[O:11])=[CH:29][CH:30]=1

Komponenten

7

Edukt 4

HCID 256687Methyl 4-(bromomethyl)benzoateHCID 2724141Tetrabutylammonium FluorideHCID 2733832Lithium HexamethyldisilazideHCID 117155522-(4-Fluorophenyl)-2-[(trimethylsilyl)oxy]acetonitrile

Produkt 1

HCID 18510220HCID 18510220, VerbindungAusbeute 65,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel4×

Versuchsvorschrift

To 2-(4-fluorophenyl)-2-[(trimethylsilyl)oxy]acetonitrile (0.500 g, 2.24 mmol) in degassed THF (11 ml) at −78° C. was added LHMDS 1M in THF (2.4 ml). To the previous reaction mixture a solution of methyl 4-(bromomethyl)benzoate (0.513 g, 2.25 mmol) in THF (2 ml) was then added. After a period of 1 h at r.t., tetrabutylammonium fluoride solution 1 M in THF (2.23 ml) was added to the reaction mixture and stirred for 10 minutes. Water was added and the mixture was extracted with ethyl acetate. The organic phase was dried over sodium sulfate and evaporated to dryness. The residue was purified by flash chromatography using hexane/ethyl acetate 30% giving 0.4 g of the title compound.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. customevaporated to dryness
  4. customThe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8d0496ff676b429dbd0e273701dac41f
Quelldatensatz
uspto-grants-2003_06
Patentnummer
US06583126B2

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