2-Nitrophenol → Benzyl 2-nitrophenyl ether

HRID 350400

Reaktionsgleichung

Reaktionsgleichung von HRID 350400
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([O-:3])=[O:2].C([O-])([O-])=O.[K+].[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C=O)C.O>[CH2:17]([O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Komponenten

6

Edukt 3

HCID 69472-NitrophenolHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Produkt 1

HCID 736266Benzyl 2-nitrophenyl etherAusbeute 89,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-nitrophenol (10.0 g, 72.0 mmol) and K2CO3 (9.96 g, 72.0 mmol) in DMF (150 mL) was added dropwise benzyl bromide (9.40 mL, 79.2 mmol) at 0° C. After being stirred at room temperature for 3 hr, the reaction mixture was diluted with water, which was extracted with Et2O. The extracts were washed with brine, dried over Na2SO4, and concentrated to dryness. Chromatography of the residue with hexane-EtOAc (2:1, v/v) as eluent gave 2-benzyloxy nitrobenzene (14.7 g, 89%) as a yellow oil. 1H-NMR (CDCl3) δ 5.24 (s, 2H), 7.04 (t, J=7.8 Hz, 1H), 7.12 (d, J=7.8 Hz, 1H), 7.31–7.50 (m, 5H), 7.51 (d, J=1.5 Hz, 1H), 7.86 (dd, J=7.8, 1.5 Hz, 1H).

Aufarbeitung

  1. extractionwas extracted with Et2O
  2. washThe extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-d5f3d3fbc1a94eb296a614a0e529ce09
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07179819B2

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