Reaktion #161183

Reaktionsgleichung

1-tert-butyl-2-(benzyloxy)-5-bromo-4-nitrobenzene

KF

KBr

methyl chlorodifluoroacetate

→

1-tert-butyl-2-(benzyloxy)-5-(trifluoromethyl)-4-nitrobenzene

Ausbeute 67.0%

Lösungsmittel

water

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled to room temperature
2. 2
   Extraktionextracted three times with EtOAc
3. 3
   WaschenThe combined organic layers were washed with brine
4. 4
   Trocknendried over anhydrous MgSO4
5. 5
   SonstigeAfter removal of the solvent
6. 6
   Sonstigethe residue was purified by column chromatography (0-5% EtOAc-Hexane)

Vorschrift

A mixture of 1-tert-butyl-2-(benzyloxy)-5-bromo-4-nitrobenzene (913 mg, 2.5 mmol), KF (291 mg, 5 mmol), KBr (595 mg, 5 mmol), CuI (570 mg, 3 mmol), methyl chlorodifluoroacetate (1.6 mL, 15 mmol) and DMF (5 mL) was stirred at 125° C. in a sealed tube overnight, cooled to room temperature, diluted with water and extracted three times with EtOAc. The combined organic layers were washed with brine and dried over anhydrous MgSO4. After removal of the solvent, the residue was purified by column chromatography (0-5% EtOAc-Hexane) to yield 1-tert-butyl-2-(benzyloxy)-5-(trifluoromethyl)-4-nitrobenzene (591 mg, 67%). 1H NMR (400 MHz, CDCl3) 7.66 (s, 1H), 7.37 (m, 5H), 7.19 (s, 1H), 5.21 (s, 2H), 1.32 (s, 9H).

Quelle