Sulfuric Acid → 3-Bromo-5-nitrophenol

HRID 418562Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 418562
N[C:2]1[C:7]([Br:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[OH:12].S(=O)(=O)(O)O.N([O-])=O.[Na+]>CCO>[Br:8][C:7]1[CH:2]=[C:3]([OH:12])[CH:4]=[C:5]([N+:9]([O-:11])=[O:10])[CH:6]=1

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 23668193Sodium NitriteHCID 49766558HCID 49766558, Verbindung

Produkt 1

HCID 104889843-Bromo-5-nitrophenolAusbeute 85,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Compound 98 (33.0 g, 0.14 mol) was treated with sulfuric acid (13.7 mL) and was refluxed in EtOH (550 mL) for 0.5 hours, followed by addition of NaNO2 (23.8 g, 0.35 mol). The resulting mixture was refluxed for additional 1 hour and the volatile was evaporated. The residue was taken up with ethyl acetate and water. The layers were separated and the organic layer was washed with water, saturated sodium bicarbonate, and brine. After removal of solvent, the residue was purified by column chromatography on silica gel to afford the title compound (26 g, 85%); 1H NMR (500 MHz, CD3OD): δ 5.00 (brs, 1H), 7.58 (dd, 1H, J=1.7, 2.3 Hz), 7.47 (t, 1H, J=2.1 Hz), 7.69 (t, 1H, J=1.9 Hz); 13C NMR (125 MHz, CD3OD): δ 110.5, 118.1, 123.7, 125.6, 151.0, 160.5; HRMS (FAB) calcd for C6H4BrNO3(M+) 216.9375. found 216.9374.

Aufarbeitung

  1. temperatureThe resulting mixture was refluxed for additional 1 hour
  2. customthe volatile was evaporated
  3. customThe layers were separated
  4. washthe organic layer was washed with water, saturated sodium bicarbonate, and brine
  5. customAfter removal of solvent
  6. customthe residue was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-633b8db969a74794b319d60e924d80ec
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093287B2

Notizen zur Reaktion

Wird geladen…