Triethylamine → HCID 86714028, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of phenol 27 (0.98 g, 1.24 mmol) in AcOH (12 mL) were added Et3N (0.37 mL, 1.86 mmol) and bromine (77 μL, 1.50 mmol) at 0° C. The mixture was stirred at 0° C. for 5 min and at room temperature for 12 hours. The reaction mixture was cooled to 0° C. and aqueous saturated NH4Cl solution (30 mL) was added to the mixture. The mixture was extracted with EtOAc (100 mL). The organic layer was washed with H2O (50 mL×2), aqueous saturated NaHCO3 solution (100 mL), dried over anhydrous MgSO4, filtered and concentrated in vacuo. The crude 2-bromo-3-chloro-4-(4-ethoxybenzyl)-6-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)phenol (28, 1.08 g) was carried on to the next step without further purification.

Provenance & Evidence