Imidazole → Benzene, 1,5-difluoro-2-methyl-4-[[tris(1-methylethyl)silyl]oxy]-

HRID 1771735Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1771735
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([CH3:9])=[CH:4][C:3]=1[OH:10].N1C=CN=C1.[CH3:16][CH:17]([Si:19](Cl)([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])[CH3:18].O>CN(C=O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([CH3:9])=[CH:4][C:3]=1[O:10][Si:19]([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:18])[CH3:16]

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 962WaterHCID 139400Triisopropylsilyl chlorideHCID 846489282,4-Difluoro-5-methylphenol

Produkt 1

HCID 89443589Benzene, 1,5-difluoro-2-methyl-4-[[tris(1-methylethyl)silyl]oxy]-Ausbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of 2,4-difluoro-5-methylphenol (780 mg, 5.41 mmol, 1.0 eq) and imidazole (442 mg, 6.5 mmol, 1.2 eq) in DMF (10 mL) at 0° C. was added TIPSCl (1.15 g, 5.95 mmol, 1.1 eq) dropwise. After the addition, the reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction was then poured into water and extracted with EtOAc. The combined organic extracts were washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo to give a crude residue, which was purified by column chromatography (petroleum ether: EtOAc, 100:1) to give the title compound as a colorless oil (1.2 g, 80%).

Aufarbeitung

  1. additionAfter the addition
  2. extractionextracted with EtOAc
  3. washThe combined organic extracts were washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto give a crude residue, which
  8. customwas purified by column chromatography (petroleum ether: EtOAc, 100:1)

Quellen und Nachweise

ORD-Eintrag
ord-673ef78312ad46849abe535ceff81b24
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09249085B2

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