Phosphorus tribromide → 1-(Bromomethyl)-2,3,5-triiodobenzene

A solution of phosphorous tribromide (3.8 ml, 40 mmol) was added dropwise to a solution of 2,3,5-triiodobenzyl alcohol 1 (9.72 g, 20 mmol) in dry tetrahydrofuran (50 ml) at 0° C. under dry nitrogen gas flow. The reaction mixture was stirred 5 minutes at 0° C., then 20 minutes at room temperature (18° C.), then cold H2O/DCM (60/60 ml) was added. The resulting aqueous phase was extracted with dichloromethane (2×10 ml). The combined organic extracts were washed with NaHCO3aq (20 ml) and H2O (20 ml) then dried (Na2SO4), filtered and concentrated. The white solid was also washed with cold methanol (45 ml). 9.35 g of 2,3,5-triiodobenzyl bromide in the form of a white clean solid was obtained in 85% yield.

1. extractionThe resulting aqueous phase was extracted with dichloromethane (2×10 ml)
2. washThe combined organic extracts were washed with NaHCO3aq (20 ml) and H2O (20 ml)
3. dry with materialthen dried (Na2SO4)
4. filtrationfiltered
5. concentrationconcentrated
6. washThe white solid was also washed with cold methanol (45 ml)

ORD record

ord-94c41136f17a4dfcbbc47ce7d429f690

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09115230B2