Hydroquinone → 2-Bromo-1,4-benzenediol

HRID 1914781Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1914781
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].[Br:9]Br.C(Cl)(Cl)Cl.CO>C(OC)(C)(C)C>[Br:9][C:7]1[CH:8]=[C:1]([OH:2])[CH:3]=[CH:4][C:5]=1[OH:6]

Komponenten

5

Edukt 3

HCID 785HydroquinoneHCID 24408BromineHCID 21584188Chloroform methanol

Produkt 1

HCID 685022-Bromo-1,4-benzenediol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 15413tert-Butyl methyl etherLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of hydroquinone Q-1 (10 g, 90.90 mmol) in MTBE (methyl tert-butyl ether) (100 mL) at −5° C. was added bromine (17.4 g, 90.90 mmol). The reaction mixture was stirred at 0° C. for 30 min. Solvent was removed in vacuo and the crude product was purified by column chromatography (SiO2, 2% MeOH—CHCl3) to afford compound Q-2 (13 g, 75%) as a solid. TLC Rf=0.6 (CHCl3-MeOH, 9:1); 1H NMR (CDCl3) δ 6.94 (app d, 1H), 6.88 (d, J=8.7 Hz, 1H), 6.72 (dd, J=8.7, 2.8 Hz, 1H), 5.19 (s, 2H) (Synlett 2000, 11, 1561-1564).

Aufarbeitung

  1. customSolvent was removed in vacuo
  2. customthe crude product was purified by column chromatography (SiO2, 2% MeOH—CHCl3)
  3. customto afford compound Q-2 (13 g, 75%) as a solid

Quellen und Nachweise

ORD-Eintrag
ord-0ccd451e670042eaa2c5e5a153cc8d9f
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08614237B2

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