1-Iodo-4-nitrobenzene → Methyl 2-(4-(4'-nitrobiphenyl-4-yl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate

To a round bottom flask containing methyl 2-(4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate (800 m g, 2.07 mmol), 1-iodo-4-nitrobenzene (619 mg, 2.49 mmol) and K3PO4 (528 mg, 2.49 mmol) was added dimethoxyethane (24 ml) at room temperature. The mixture was stirred at room temperature and degassed after the addition of EtOH (8 ml) and water (3.2 ml). PdCl2(dppf) dichloromethane adduct (85 mg, 0.10 mmol) was added and the mixture was heated to 8° C. in an oil bath for overnight. The reaction mixture was then concentrated to dryness and taken up in DCM. The slurry was dried over sodium sulfate and filtered through a pad of celite. The filtrate was concentrated and purified by column chromatography affording the title compound as off-white solid (624 mg, 79% yield). LC/MS, ESI-MS(+): 382.4, RT: 1.49 (Condition E).

1. customdegassed
2. additionafter the addition of EtOH (8 ml) and water (3.2 ml)
3. temperaturethe mixture was heated to 8° C. in an oil bath for overnight
4. concentrationThe reaction mixture was then concentrated to dryness
5. dry with materialThe slurry was dried over sodium sulfate
6. filtrationfiltered through a pad of celite
7. concentrationThe filtrate was concentrated
8. custompurified by column chromatography

ORD record

ord-58a984f7534f480da937a98253996e92

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08993619B2