Reaktion #161190

Reaktionsgleichung

1-tert-butyl-2-methoxy-5-bromo-4-nitrobenzene

KF

KBr

methyl chlorodifluoroacetate

→

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

Ausbeute 61.6%

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-methoxy-5-bromo-4-nitrobenzene (867 mg, 3.0 mmol), KF (348 mg, 6 mmol), KBr (714 mg, 6 mmol), CuI (684 mg, 3.6 mmol), methyl chlorodifluoroacetate (2.2 mL, 21.0 mmol) in 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-methoxy-5-(trifluoromethyl)-4-nitrobenzene (512 mg, 61%). 1H NMR (400 MHz, CDCl3) δ 7.60 (s, 1H), 7.29 (s, 1H), 3.90 (s, 3H), 1.33 (s, 9H).

Quelle