Ethyl Bromide → 1-Ethoxy-2,5-difluoro-4-nitrobenzene

HRID 1811549Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1811549
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([F:11])=[CH:4][C:3]=1[OH:12].C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][CH3:21].ICC>C(#N)C>[CH2:20]([O:12][C:3]1[CH:4]=[C:5]([F:11])[C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[F:1])[CH3:21]

Komponenten

6

Edukt 4

HCID 6332Ethyl BromideHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 27824902,5-Difluoro-4-nitrophenol

Produkt 1

HCID 685658171-Ethoxy-2,5-difluoro-4-nitrobenzeneAusbeute 88,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of 2,5-difluoro-4-nitro-phenol (4.86 g, 28.2 mmol) in acetonitrile (50 mL), potassium carbonate (4.7 g, 34 mmol) and bromoethane (4.21 mL, 56.4 mmol) were added. After stirring at 70° C. for 3.5 hours, iodoethane (2.73, 33.8 mmol) was added and mixture was stirred at 80° C. After 20 hours, mixture was concentrated and extracted with methylene chloride and 2M NaOH solution. Organic phases were dried over magnesium sulfate, filtered, and concentrated to give 1-ethoxy-2,5-difluoro-4-nitro-benzene as a yellow solid (5.05 g, 88%). 1HNMR (CDCl3, 400 MHz) δ 7.92-7.88 (m, 1H), 6.82-6.78 (m, 1H), 4.21-4.16 (q, 1H), 4.13-4.07 (q, J=7.0 Hz, 2H), 1.54-1.51 (t, J=7.0 Hz, 3H).

Aufarbeitung

  1. stirringmixture was stirred at 80° C
  2. waitAfter 20 hours
  3. concentrationmixture was concentrated
  4. extractionextracted with methylene chloride and 2M NaOH solution
  5. dry with materialOrganic phases were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-286ff2a7d1a84cddbf78d767383003a3
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362248B2

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