1,2-Dimethoxyethane → 2',4'-Dichloro-4-hydroxy[1,1'-biphenyl]-3-carbaldehyde

To a mixture of 5-bromosalicyaldehyde (30.0 g, 0.15 mol), 2,4-dichlorophenylboronic acid (32.0 g, 0.17 mol) and sodium carbonate (24.0 g, 0.23 mol) is added 1,2-dimethoxyethane (225 ml) and distilled water (75 ml), and the suspension is stirred under a nitrogen atmosphere. To this mixture is then added [1,1′-bis(diphenylphosphino)ferrocene]palladium(II)chloride (4.5 g, 7.5 mmol), followed by heating at reflux overnight. After cooling to room temperature and dilution with distilled water (500 ml) and dichloromethane (500 ml), the two phases are separated, and the aqueous phase extracted again with dichloromethane (2×500 ml). Organic fractions are combined, washed with brine (800 ml) then dried over magnesium sulphate. The suspension is filtered and the filtrate concentrated in vacuo. Then crude material is finally purified by flash column purification (10% ethyl acetate in isohexane eluant) to afford 2′,4′-dichloro-4-hydroxybiphenyl-3-carbaldehyde (32.73 g, 82%) as a pale yellow solid.

1. distillationdistilled water (75 ml)
2. temperatureby heating
3. temperatureat reflux overnight
4. customdilution with distilled water (500 ml) and dichloromethane (500 ml), the two phases are separated
5. extractionthe aqueous phase extracted again with dichloromethane (2×500 ml)
6. washwashed with brine (800 ml)
7. dry with materialthen dried over magnesium sulphate
8. filtrationThe suspension is filtered
9. concentrationthe filtrate concentrated in vacuo
10. customThen crude material is finally purified by flash column purification (10% ethyl acetate in isohexane eluant)

ORD-Eintrag

ord-26d2943926b34028a3b7a33543ed66e7

Quelldatensatz

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08680299B2