Phenethyl bromide → 4-(3-Phenylpropyl)pyridine

To a solution of 2.32 g (25.0 mmol) of 4-picoline in 40 mL of THF at −78° C. was slowly added 17.5 mL of a 1.6 M solution of n-butyllithium in hexanes (28.0 mmol). The reaction mixture was allowed to warm to rt and stirred for 1 h at rt. This reaction mixture was added via cannula to a solution of 6.8 mL (50.0 mmol) of (2-bromoethyl)benzene in 30 mL of THF at −50° C. The mixture was warmed to rt, quenched by the addition of 50 mL of H2O and extracted with ether. The combined organic fractions were extracted with 2N HCl. The combined aqueous fractions were brought to pH=12 with 5N NaOH and again extracted with ether. The combined ether layers were washed with sat'd NaCl solution, dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, hexanes:ethyl acetate=3:1) to give the title compound.

1. customat −78° C.
2. temperatureThe mixture was warmed to rt
3. customquenched by the addition of 50 mL of H2O
4. extractionextracted with ether
5. extractionThe combined organic fractions were extracted with 2N HCl
6. extractionagain extracted with ether
7. washThe combined ether layers were washed with sat'd NaCl solution
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. concentrationthe filtrate was concentrated
11. customThe residue was purified by chromatography (silica, hexanes:ethyl acetate=3:1)

ORD record

ord-a011ab27953a465f859275b32a9747fb

Source dataset

uspto-grants-2001_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06303593B1