Imidazole → Phenol, 4-(4-bromobutyl)-

HRID 1586317Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1586317
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20]Br.[OH:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][CH2:31][CH2:32]O)=[CH:25][CH:24]=1.N1C=CN=C1>C(Cl)Cl>[OH:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][CH2:31][CH2:32][Br:20])=[CH:25][CH:24]=1

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 11776TriphenylphosphineHCID 24408BromineHCID 133925134-(4-Hydroxybutyl)phenol

Produkt 1

HCID 11128076Phenol, 4-(4-bromobutyl)-Ausbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of triphenylphosphine (144.1 mmole, 37.80 g) in methylene chloride (556 ml) was treated with bromine (144.1 mmole, 23.03 g) until a pale yellow color persisted. After stirring approximately 15 minutes, a solution of 4-(4-hydroxyphenyl)butanol (96.1 mmole, 15.97 g) and imidazole (192.2 mmole, 13.08 g) in methylene chloride (355 ml) was added over a 15 minute period. Approximately 4 hours later, the reaction suspension was filtered and the filtrate was reduced in volume. To the reduced filtrate was added silica gel and the suspension was reduced to dryness. This material was filtered and the first six fractions were eluted with 10% ethyl acetate:hexane. Fractions 7 through 12 were eluted with 20% ethyl acetate:hexane. Fractions 7 through 10 were combined, reduced in volume, dried over sodium sulfate, filtered and concentrated in vacuo to afford 19.32 g (88%) of the title compound as an oil.

Aufarbeitung

  1. filtrationApproximately 4 hours later, the reaction suspension was filtered
  2. additionTo the reduced filtrate was added silica gel
  3. filtrationThis material was filtered
  4. washthe first six fractions were eluted with 10% ethyl acetate
  5. washFractions 7 through 12 were eluted with 20% ethyl acetate
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-77848eb60cab45e4bf3de75dab0e171a
Quelldatensatz
uspto-grants-1999_08
Patentnummer
US05942530

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