Bromine → HCID 58536745, compound

Participants

Reaction Steps

step b—To a solution of 109 (3 g, 10.7 mmol) and HOAc (40 mL) stirred at RT under N2 was added dropwise via cannula a solution of bromine (1.88 g, 605 μL, 11.7 mmol) in HOAc (20.0 mL) over 20 min. The solution was stirred for 1 h at RT then warmed reaction to 50° C. and stirred 1 h. An aliquot of neat bromine (100 μL) was added and heating continued. The total heating time was 2.5 h. The reaction mixture was poured over ice, partitioned between EtOAc and H2O and aqueous phase was neutralized with satd. aq. NaHCO3. The organic layer was separated, washed with brine, dried (MgSO4), filtered and concentrated. The product was purified by SiO2 chromatography eluting with hexanes to afford 3.8 g (quantitative) of 110.

Provenance & Evidence