4-Bromophenol → 18085-61-5

Temperatur

100 °C

A mixture of 3-iodopyridine (602 mg, 2.94 mmol), 4-bromophenol (560 mg, 3.24 mmol), CuBr (23 mg, 0.16 mmol), 1-(pyridin-2-yl)propan-2-one (53 mg, 0.39 mmol), Cs2CO3 (1.92 g, 5.89 mmol), and DMSO (6 mL) was degassed with three vacuum/N2 cycles, heated at 100° C. for 9 h, and then stirred at rt overnight. The reaction was filtered through Celite with EtOAc. The filtrate was washed with H2O (100 mL) and brine (100 mL). The aqueous wash was back extracted with EtOAc (3×40 mL). The organic extracts were combined, dried (MgSO4), filtered, concentrated, and purified by silica gel chromatography (0%-20% EtOAc in hexanes) to give 250 mg of 3-(4-bromophenoxy)pyridine as a clear liquid. 1H NMR (400 MHz, DMSO-d6): δ 8.39-8.42 (m, 2H), 7.58-7.61 (m, 2H), 7.43-7.51 (m, 2H), 7.02-7.07 (m, 2H).

1. customwas degassed with three vacuum/N2 cycles
2. filtrationThe reaction was filtered through Celite with EtOAc
3. washThe filtrate was washed with H2O (100 mL) and brine (100 mL)
4. washThe aqueous wash
5. extractionwas back extracted with EtOAc (3×40 mL)
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated
9. custompurified by silica gel chromatography (0%-20% EtOAc in hexanes)

ORD-Eintrag

ord-3a1afc2dca1f43a0bf42b99e1e975abb

Quelldatensatz

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09399646B2