Trifluoroacetic acid → Methyl 3-(4-bromophenyl)cyclobutane-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence