Bromine → HCID 86714033, compound

Participants

Reaction Steps

To a mixture of 5-chloro-4-(4-ethylbenzyl)-2-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)phenol (3.0 g, 3.90 mmol) and TEA (1.63 mL) in acetic acid (20.1 mL) was added dropwise bromine (0.30 mL, 5.85 mmol) at 0° C. under nitrogen atmosphere. After stirring for 2 h at rt, the reaction mixture was quenched with saturated NH4Cl solution (50 mL) and extracted with EtOAc (100 mL). The organic layer was washed with brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography to provide the compound 32 (2.99 g, 3.53 mmol, 90%).

Provenance & Evidence