Carbon tetrabromide → HCID 18700084, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 4-(N-tert-butyloxy-carbonyl-4-piperidinyloxy)-2-trifluoromethylbenzyl alcohol (0.63 g, 1.7 mmol) from Step 3 above in ether (10 mL) at 0° C. was added CBr4 (0.85 g, 2.6 mmol) and triphenylphosphine (0.68 g, 2.6 mmol). The mixture was stirred at 0° C. for 30 min and then at ambient temperature for 14 h. The ether solution was decanted away from the gummy precipitate of triphenylphosphine oxide that had formed and the solvent was removed unde reduced pressure. The residue was purified by pressurized silica gel column chromatography using 5% EtOAc:hexanes as eluant to give 4-(N-tert-butyloxycarbonyl-4-piperidinyloxy)-2-trifluoromethylbenzyl bromide as a colorless gum (HPLC retention time=12.6 min (method A)).

Provenance & Evidence