Trifluoroacetic acid → Methyl 3-(4-bromophenyl)cyclobutane-1-carboxylate
반응식
FC(F)(F)C(O)=O.[Br:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2(O)[CH2:18][CH:17]([C:19]([O:21][CH3:22])=[O:20])[CH2:16]2)=[CH:11][CH:10]=1.[SiH](CC)(CC)CC>>[Br:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]2[CH2:16][CH:17]([C:19]([O:21][CH3:22])=[O:20])[CH2:18]2)=[CH:13][CH:14]=1참가 물질
4
반응 조건
- 온도
- 17.5 °C
실험 절차
Into a 20-L 4-necked round-bottom flask was placed trifluoroacetic acid (12 L), methyl 3-(4-bromophenyl)-3-hydroxycyclobutane-1-carboxylate (2330 g, 8.17 mol, 1.00 equiv), followed by the addition of Et3SiH (3556 g, 30.58 mol, 5.00 equiv) dropwise with stirring at 10-25° C. The resulting solution was stirred at room temperature for 0.5 h, concentrated under vacuum, diluted with 8 L of H2O and extracted with 1×8 L of ethyl acetate. The organic layers were combined, washed with 1×3 L of saturated aqueous sodium bicarbonate and 1×2 L of brine, dried over anhydrous sodium sulfate and concentrated under vacuum to afford 2175 g (crude) of methyl 3-(4-bromophenyl)cyclobutane-1-carboxylate as an orange oil.