Phosphorus tribromide → 2-Iodobenzyl Bromide

Temperature

0 °C

To a dry 100 mL 3-necked flask equipped with a nitrogen inlet and a magnetic stirrer were added 5.00 g of 2-iodobenzyl alcohol (Aldrich) and 20 mL of anhydrous CH2Cl2. The resulting suspension was cooled to 0° C. and treated with 0.71 mL of PBr3 (Aldrich) by dropwise addition over a 2 minute period. The solid slowly dissolved giving a light yellow solution which was stirred under nitrogen at 0° C. for 2 h and then allowed to warm to RT with continued stirring for 18 h. The solution was concentrated in vacuo to dryness and the residue was dissolved in 60 mL of ethyl ether. The ether solution was washed with ice cold 5% aqueous NaHCO3 (3×50 mL), dried over anhydrous Na2SO4, and concentrated in vacuo to afford 5.65 g (89%) of 2-iodobenzyl bromide as a white crystalline solid, m.p. 52-54° C.

1. customTo a dry 100 mL 3-necked flask equipped with a nitrogen inlet and a magnetic stirrer
2. dissolutionThe solid slowly dissolved
3. customgiving a light yellow solution which
4. temperatureto warm to RT
5. stirringwith continued stirring for 18 h
6. concentrationThe solution was concentrated in vacuo to dryness
7. dissolutionthe residue was dissolved in 60 mL of ethyl ether
8. washThe ether solution was washed with ice cold 5% aqueous NaHCO3 (3×50 mL)
9. dry with materialdried over anhydrous Na2SO4
10. concentrationconcentrated in vacuo

ORD record

ord-fa38e930c52346538a3e999cf29a7c62

Source dataset

uspto-grants-2000_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06140100