Boron tribromide → 4,4'-Dihydroxybenzil

HRID 1620357

Reaktionsgleichung

Reaktionsgleichung von HRID 1620357
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:20])[C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18]C)=[CH:14][CH:13]=2)=[O:11])=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9](=[O:20])[C:10]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)=[O:11])=[CH:7][CH:8]=1

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 710434,4'-Dimethoxybenzil2×

Produkt 1

HCID 4582044,4'-Dihydroxybenzil

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

1,2-bis(4-methoxyphenyl)ethane-1,2-dione (5 g, 18.52 mmol) was dissolved in CH2Cl2 and cooled to −78° C. (solid occurred again). BBr3 (8.3 m, 87.82 mmol) was added and mixture was allowed to warm to room temperature and stirred for 15 hrs. TLC check showed 1,2-bis(4-methoxyphenyl)ethane-1,2-dione completely disappeared. The reaction mixture was poured into ice, extracted by EtOAc, washed with NaCl solution, dried over MgSO4. The solvent was removed by vacuum, and the residue was purified by column chromatography to give compound 5, 1,2-bis(4-hydroxyphenyl)ethane-1,2-dione, as confirmed by the following nuclear magnetic resonance (NMR) data obtained therefrom: 1H NMR (500 MHz, DMSO): δ 10.8 (s, 2H), 7.71 (d, J=8.8 MHz, 4H), 6.90 (d, J=8.8 MHz, 4H) ppm.

Aufarbeitung

  1. temperatureto warm to room temperature
  2. additionThe reaction mixture was poured into ice
  3. extractionextracted by EtOAc
  4. washwashed with NaCl solution
  5. dry with materialdried over MgSO4
  6. customThe solvent was removed by vacuum
  7. customthe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8f58a185f81d4038ba6863ed558e69ef
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772443B2

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