Nitrogen → 4-[2-(4-Butylphenyl)ethynyl]benzaldehyde

To a dry 2 L three-necked flask under a flow of N2 containing 1-bromo-4-[(4-butylphenyl) ethynyl] benzene (VIIe) (100 g; 0.319 mol) in dry THF (1000 mL) at −78° C. was added n-BuLi (2.5M in hexane, 153.25 mL, 0.383 mol) and the reaction mixture was stirred at this temperature for 2 h. The reaction mixture went dark-green after 5 minutes of the addition of butyl lithium. To this reaction mixture was added DMF (29.56 mL, 0.383 mol) and the resulting mixture was stirred for an additional 1 h at −78° C. The reaction mixture turned black-blue after the addition of DMF. The reaction mixture was then quenched with 1.5M HCl (750 ml) at this temperature and the product was extracted with MTBE (3×500 mL). The combined organic layer were washed with 10% sodium bicarbonate solution (500 ml), water, brine and dried. The solvent was evaporated under reduced pressure to afford the title compound (m=65 g) as a white solid in a 77% yield. Melting point: 76-78° C.

1. stirringthe resulting mixture was stirred for an additional 1 h at −78° C
2. customThe reaction mixture was then quenched with 1.5M HCl (750 ml) at this temperature
3. extractionthe product was extracted with MTBE (3×500 mL)
4. washThe combined organic layer were washed with 10% sodium bicarbonate solution (500 ml), water, brine
5. customdried
6. customThe solvent was evaporated under reduced pressure

ORD record

ord-7c7a0c8975e44cafafa27a3ecb208a76

Source dataset

uspto-grants-2009_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07479575B2