Acetonitrile → 1-(Allyloxy)-2-bromo-5-chloro-4-(4-ethoxybenzyl)benzene

Temperatur

0 °C

To a stirred −10° C. solution of (5-Bromo-2-chloro-4-methoxyphenyl)(4-ethoxyphenyl)methanone (54.3 mmol) from Step 4 in dichloromethane (150 mL)/acetonitrile (150 mL) was added triethylsilane (20 mL, 109 mmol) followed by boron trifluoride diethyl etherate (16 mL, 109 mmol) at −10° C. The solution was allowed to warm to 0° C. over 2 h prior to quenching with saturated sodium carbonate solution. After removal of organic volatiles under reduced pressure, the residue was partitioned between ethyl acetate and water. Following extraction of the aqueous layer with ethyl acetate, the combined organic layers were washed with water prior to drying over magnesium sulfate. Filtration and concentration under reduced pressure yielded the title compound as a yellowish solid which was used without further purification.

1. customto quenching with saturated sodium carbonate solution
2. customAfter removal of organic volatiles under reduced pressure
3. customthe residue was partitioned between ethyl acetate and water
4. extractionextraction of the aqueous layer with ethyl acetate
5. washthe combined organic layers were washed with water
6. dry with materialto drying over magnesium sulfate
7. filtrationFiltration and concentration under reduced pressure

ORD-Eintrag

ord-4b6402c0fda64e8c95ec0c46eac0204f

Quelldatensatz

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08921412B2