Reaktion #160620

Reaktionsgleichung

3,4,5-trifluoro-2-nitrophenol

Ph3P

2-methoxy-ethanol

diisopropyl azodicarboxylate

→

titled product

1,2,3-Trifluoro-5-(2-methoxyethoxy)-4-nitrobenzene

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added at 0° C.
2. 2
   SonstigeThe volatiles were evaporated
3. 3
   workup.DISSOLUTIONthe residue was dissolved in CH2Cl2 (100 ml)
4. 4
   Waschenthe organic layer was washed with water (100 ml), brine (100 ml)
5. 5
   Trocknendried (MgSO4)
6. 6
   Sonstigeevaporated
7. 7
   SonstigeThe residue obtained
8. 8
   Sonstigewas purified over flash silica gel chromatography

Vorschrift

To a mixture of 3,4,5-trifluoro-2-nitrophenol (1.93, 10 mmol), Ph3P (3.93 g, 15 mmol), and 2-methoxy-ethanol (1.18 ml, 15 mmol) in anhydrous THF (25 ml) a solution of diisopropyl azodicarboxylate (2.91 ml, 15 mmol) in THF (5 ml) was added at 0° C. and the reaction mixture was stirred at room temperature for 16 h. The volatiles were evaporated and the residue was dissolved in CH2Cl2 (100 ml) and the organic layer was washed with water (100 ml), brine (100 ml) dried (MgSO4) and evaporated. The residue obtained was purified over flash silica gel chromatography to obtain the titled product in 68% (1.70 g) yield. 1H NMR (300 MHz, CDCl3): δ 6.78 (ddd, J=2.4, 6.4, 11.7 Hz, 1H), 4.19 (t, J=4.5. Hz, 2H), 3.72 (t, J=4.5 Hz, 2H), 3.39 (s, 3H).

Quelle