Benzyl Bromide → 4-(Benzyloxy)-3-bromophenol

HRID 855089

Reaktionsgleichung

Reaktionsgleichung von HRID 855089
C([O-])([O-])=O.[K+].[K+].[Br:7][C:8]1[CH:13]=[C:12]([OH:14])[CH:11]=[CH:10][C:9]=1[OH:15].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[Cl-].[NH4+]>CO>[CH2:16]([O:15][C:9]1[CH:10]=[CH:11][C:12]([OH:14])=[CH:13][C:8]=1[Br:7])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

6

Edukt 4

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 685022-Bromo-1,4-benzenediol

Produkt 1

HCID 132534114-(Benzyloxy)-3-bromophenol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

To a mixture of MeOH (50 mL) and K2CO3 (49.36 g, 357 mmole) at r.t was dripped commercially available 2-bromobenzene-1,4-diol (15 g, 79 mmole) in MeOH (25 mL), followed by the syringe addition of benzyl bromide (14.93 g, 10.38 mL). The resulting mixture was refluxed for 8 hours. The reaction was cooled to RT and poured into saturated aqueous ammonium chloride (500 mL) and extracted with ethyl acetate (2×150). The combined organic phases were washed with aqueous NaHCO3 solution (2×150 mL), aqueous 1N HCl solution (2×150 mL), and brine (2×150 mL), dried over Na2SO4, filtered and concentrated in vacuo. The crude material was subjected to flash chromatography (Silica, 10% Ethyl acetate/Hexane). ESLRMS m/z 280.9 (M+H).

Aufarbeitung

  1. temperatureThe resulting mixture was refluxed for 8 hours
  2. extractionextracted with ethyl acetate (2×150)
  3. washThe combined organic phases were washed with aqueous NaHCO3 solution (2×150 mL), aqueous 1N HCl solution (2×150 mL), and brine (2×150 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1d63b9a29149496f8a7db3f39e9941c1
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07259266B2

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