Cesium carbonate → 4-Bromo-2-chloro-1-[(3-methyl-3-buten-1-yl)thio]benzene

Temperatur

85 °C

To a mixture of 4-bromo-2-chlorobenzenethiol (1.68 g, 7.54 mmol) and Cs2CO3 (4.09 g, 12.6 mmol) in DMF (8.98 mL) at room temperature was added 3-methylbut-3-en-1-yl diphenyl phosphate (2.00 g, 6.28 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 diluted with water (20.0 mL). The resulting mixture was extracted with EtOAc:hexanes mixture (1:1, 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 0-10% EtOAc/hexanes to give the desired product as a colorless oil.

1. customsynthesized
2. temperatureto cool to room temperature
3. extractionThe resulting mixture was extracted with EtOAc
4. dry with materialhexanes mixture (1:1, 75.0 mL, 2×) and the 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 0-10% EtOAc/hexanes

ORD-Eintrag

ord-52d20454894e4b9c9c46e84ecc2b5e20

Quelldatensatz

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08742110B2