Triphenylphosphine dibromide → 1-(2-Bromoethyl)-3-chlorobenzene

According to Scheme 11, a solution of 3-chlorophenethyl alcohol (5 g, 32 mmol) in 50 mL of dry MeCN was treated with dibromotriphenylphosphorane (13.54 g, 32 mmol) for 24 h. The reaction mixture was filtered and the solvent was removed in vacuo. The residue was triturated with hexane and filtered. Evaporation of the solvent provided 6.5 g of 3-chlorophenethyl bromide. A solution of the bromide (6.5 g, 29.6 mmol) in 50 mL of dry DMSO containing NaCN (2.17 g, 44 mmol) was heated to 100° C. overnight. The reaction mixture was diluted with water and extracted with ether. The ether layer was washed with water, dried and the solvent was removed in vacuo. Chromatography (silica gel, hexane:ethyl acetate, 4:1) provided 3.7 g of nitrile 89.

1. filtrationThe reaction mixture was filtered
2. customthe solvent was removed in vacuo
3. customThe residue was triturated with hexane
4. filtrationfiltered
5. customEvaporation of the solvent

ORD record

ord-302c44fcd1f6477180437537bb766e8d

Source dataset

uspto-grants-2005_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06919347B2