Phosphorus tribromide → 2-Iodobenzyl Bromide

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence