2-Methyl-4-nitrophenol → 2-Bromo-6-methyl-4-nitrophenol

HRID 510251Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 510251
[Br:1]Br.[CH3:3][C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[OH:13]>CC(O)=O>[Br:1][C:6]1[CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=[C:4]([CH3:3])[C:5]=1[OH:13]

Komponenten

4

Edukt 2

HCID 74422-Methyl-4-nitrophenolHCID 24408Bromine

Produkt 1

HCID 203754122-Bromo-6-methyl-4-nitrophenolAusbeute 80,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

Br2 (122.2 g, 0.765 mol) was added into a solution of 2-methyl-4-nitrophenol (90.0 g, 0.588 mol) in HOAc (1.17 L) at room temperature. The resulting solution was stirred at room temperature for 4 h. TLC showed the reaction was complete. The solution was added into ice-water (3 L) slowly and filtered. The filter cake was dissolved into EA (2.5 L) and washed with saturated NaHSO3 (3×500 mL). The EtOAc layer was dried over anhydrous Na2SO4, filtered and concentrated in vacuo to afford 2-bromo-6-methyl-4-nitrophenol (110 g, 80%) as yellow solid. 1H-NMR: 400 MHz, (CDCl3) δ: 8.30 (d, J=2.0 Hz, 1H), 8.05 (s, 1H), 6.22 (s, broad, 1H), 2.41 (s, 3H).

Aufarbeitung

  1. filtrationfiltered
  2. dissolutionThe filter cake was dissolved into EA (2.5 L)
  3. washwashed with saturated NaHSO3 (3×500 mL)
  4. dry with materialThe EtOAc layer was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d1aa1428b6134bffb974c1ef5fcb20be
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096586B2

Notizen zur Reaktion

Wird geladen…