Cesium carbonate → 4-Bromo-2-chloro-1-[(3-methylbut-3-en-1-yl)oxy]benzene

Temperatur

85 °C

To a mixture of 4-bromo-2-chlorophenol (0.98 g, 4.71 mmol), and Cs2CO3 (2.05 g, 6.28 mmol) in DMF (4.49 mL) at room temperature was added 3-methylbut-3-en-1-yl diphenyl phosphate (1.00 g, 3.14 mmol, synthesized according to a procedure in U.S. Pat. No. 5,006,550, 9 Apr. 1991) dropwise via a syringe. The reaction mixture was heated to 85° C. for 1 hour. It was then allowed to cool to room temperature and was diluted with water (20.0 mL). The resulting mixture was extracted with hexane (75.0 mL, 2×) and the combined organic layers were dried over Na2SO4, filtered, and concentrated under vacuum. The crude mixture was purified by silica gel chromatography eluting with 0-5% EtOAc/hexanes to give the title compound as a colorless oil.

1. customsynthesized
2. temperatureto cool to room temperature
3. extractionThe resulting mixture was extracted with hexane (75.0 mL, 2×)
4. dry with materialthe combined organic layers were dried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated under vacuum
7. customThe crude mixture was purified by silica gel chromatography
8. washeluting with 0-5% EtOAc/hexanes

ORD-Eintrag

ord-b6f475f2bd914eabb6253a1e73646b72

Quelldatensatz

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08742110B2