(1,1'-Biphenyl)-4-carboxaldehyde → 1,1'-Biphenyl, ethenyl-

To a suspension of methyltriphenylphosphonium bromide (5.10 g, 14.27 mmol) in THF (26 mL) was slowly added potassium tert-butoxide (1M solution in THF, 14.27 mL) over ˜20 min at 0° C. The reaction mixture was allowed to warm up to room temperature and stirred for 10 min. The mixture was cooled to 0° C. and a solution of 4-biphenylcarbaldehyde (2.0 g, 10.98 mmol) in THF (9 mL) was added over 20 min. The reaction mixture was allowed to warm up to room temperature and stirred for ˜19 hour. The mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was dissolved/suspended in DCM and filtered through a silica pad and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography [SiO2, 80 g, EtOAc/heptane] to provide vinylbiphenyl (1.845 g) as a white solid. LCMS Rt 0.79 min.

1. customover ˜20 min
2. customat 0° C
3. temperatureThe mixture was cooled to 0° C.
4. temperatureto warm up to room temperature
5. stirringstirred for ˜19 hour
6. filtrationThe mixture was filtered
7. concentrationthe filtrate was concentrated under reduced pressure
8. filtrationfiltered through a silica pad
9. concentrationthe filtrate was concentrated under reduced pressure
10. customThe residue was purified by column chromatography [SiO2, 80 g, EtOAc/heptane]

ORD record

ord-9c641cb29a1b41e2b541cca6de0f94d5

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08957068B2