반응 #161183

반응 방정식

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

KF

KBr

methyl chlorodifluoroacetate

→

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

수율 67.0%

용매

water

DMF

반응 조건

후처리

1. 1
   온도cooled to room temperature
2. 2
   추출extracted three times with EtOAc
3. 3
   세척The combined organic layers were washed with brine
4. 4
   건조dried over anhydrous MgSO4
5. 5
   기타After removal of the solvent
6. 6
   기타the residue was purified by column chromatography (0-5% EtOAc-Hexane)

실험 절차

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).

출처