Iodine → HCID 22620867, compound

200 g (0.8 mol) of 2-bromobenzylbromide and 800 ml of dry THF were placed in a 2 L round bottom flask equipped with mechanical stirrer. Keeping this mixture at 20° C., 9.8 g of Mg (0.4 mol) was added in small portions. The reaction was started with a trace of iodine and stirred for 20 h. Workup was done by decanting the organic layer from the salts and washing the salts with 4 portions of 50 ml THF. The organic layers were combined and concentrated in vacuo. The resulting solid was dissolved in 400 ml dichloromethane and washed with 400 ml 5% HCl and twice with 200 ml water. The organic layer was separated from the aqueous layer, dried with MgSO4, and concentrated in vacuo. Crystallization was done from ethanol. The product was isolated as white crystals (52 g). The remaining supernatant liquor was distilled to remove the starting material and by-products. The distilled product was crystallized from pentane and afforded an additional 12.6 g of product. Total product 64.6 g. Yield 48%.

1. customequipped with mechanical stirrer
2. customat 20° C.
3. customby decanting the organic layer from the salts
4. washwashing the salts with 4 portions of 50 ml THF
5. concentrationconcentrated in vacuo
6. dissolutionThe resulting solid was dissolved in 400 ml dichloromethane
7. washwashed with 400 ml 5% HCl and twice with 200 ml water
8. customThe organic layer was separated from the aqueous layer
9. dry with materialdried with MgSO4
10. concentrationconcentrated in vacuo
11. customCrystallization

ORD record

ord-94ab9eb8df72452092bbb81e488b2523

Source dataset

uspto-grants-2002_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06369254B1