Ethyl bromoacetate → Ethyl 2-(4-bromo-2-nitrophenoxy)acetate

HRID 570152Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 570152
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>CN(C)C=O>[CH2:23]([O:22][C:20](=[O:21])[CH2:19][O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=1[N+:9]([O-:11])=[O:10])[CH3:24]

Komponenten

5

Edukt 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 243644-Bromo-2-nitrophenol

Produkt 1

HCID 24903547Ethyl 2-(4-bromo-2-nitrophenoxy)acetateAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 4-bromo-2-nitro-phenol (3.28 g, 15.0 mmol, 1 equiv) in dimethylformamide (40 mL) at 23° C. was added potassium carbonate (4.14 g, 30 mmol, 2 equiv) followed by ethyl bromoacetate (1.84 mL, 16.6 mmol, 1.1 equiv). The resulting mixture was warmed to 60° C. (oil bath) for 90 min then cooled to 23° C. The reaction mixture was partitioned between ethyl acetate:heptane (1:1) and water (100 mL each). The organic layer was separated and washed successively with water, saturated brine solution (100 ml, each) then dried (MgSO4), filtered and concentrated to give 4.50 g (11.5 mmol, 77%) of the product as a yellow oil.

Aufarbeitung

  1. temperaturethen cooled to 23° C
  2. customThe reaction mixture was partitioned between ethyl acetate:heptane (1:1) and water (100 mL each)
  3. customThe organic layer was separated
  4. washwashed successively with water, saturated brine solution (100 ml
  5. dry with materialeach) then dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-92a8b32be51c464ba385f2f4b6fddb48
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09023843B2

Notizen zur Reaktion

Wird geladen…