Cesium carbonate → HCID 67538572, compound

To a solution of 5-bromo-2-fluorophenol (19.63 g, 102.8 mmol) in DMF (410 mL) was added Cs2CO3 (40.19 g, 123.36 mmol, 1.2 eq.) followed by 4-bromo-1-butene (15.26 g, 11.48 mL, 113.06 mmol, 1.1 eq.). The mixture was stirred overnight at a temperature between 50 and 60° C. Then additional amounts of Cs2CO3 and the bromoalkene (20.1 g, 0.6 eq.) and (7.53 g, 5.74 mL, 0.55 eq.) respectively were added to the reaction mixture and heating was continued overnight. The mixture was cooled to room temperature and diluted with water. The aqueous mixture was extracted with EtOAc and the aqueous layer was separated and extracted once with EtOAc. The combined organic layers were washed with water, dried over Na2SO4, filtered, and concentrated onto 50 g Celite. Flash chromatography (SiO2, Hexanes to 30% EtOAc 70% Hexanes) provided 11.87 g, 47%, of the title compound as a colorless to light yellow oil.

1. temperatureheating
2. waitwas continued overnight
3. extractionThe aqueous mixture was extracted with EtOAc
4. customthe aqueous layer was separated
5. extractionextracted once with EtOAc
6. washThe combined organic layers were washed with water
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated onto 50 g Celite
10. customFlash chromatography (SiO2, Hexanes to 30% EtOAc 70% Hexanes) provided 11.87 g, 47%

ORD record

ord-10916e12703644ad95446613725443ed

Source dataset

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07723368B2