Pyridine → 1-(3-Bromopropyl)-4-chlorobenzene

To a stirred solution of 4.15 g (15.8 mmol) of triphenylphosphine in 100 ml of toluene at 0° C., 1.51 ml (15.8 mmol) of bromine was added dropwise. This mixture was stirred for 3 hours then a solution of 3.90 g (22.9 mmol) of Part (a) alcohol and 1.63 ml (15.8 mmol) of pyridine in 20 ml of toluene was added. A solution of 25 ml hexane and 25 ml diethyl ether was added, and a brown mass was formed. The liquid was decanted and concentrated in vacuo. The residue was triturated with hexane:ethyl acetate and triphenylphosphine oxide was precipitated. The solid was filtered and the filtrate was concentrated in vacuo to give a yellow oil. The oil was purified by flash chromatography to obtain 1.80 g 7.72 mmol, 49%) of the desired product.

1. customa brown mass was formed
2. customThe liquid was decanted
3. concentrationconcentrated in vacuo
4. customThe residue was triturated with hexane
5. customethyl acetate and triphenylphosphine oxide was precipitated
6. filtrationThe solid was filtered
7. concentrationthe filtrate was concentrated in vacuo
8. customto give a yellow oil
9. customThe oil was purified by flash chromatography

ORD record

ord-f981a7584a7c405fa6944a7a69f0aa36

Source dataset

uspto-grants-1992_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05100889