Water → (2,6-Diisopropylphenyl)[1-(2'-methoxybiphenyl-3-yl)ethylidene]amine

Temperature

-70 °C

To a solution of 2.78 g (7.75 mmol) of 13 in 30 mL of THF, 3.10 mL (7.75 mmol) of 2.5 M nBuLi in hexanes was added at −100° C. The reaction mixture was stirred for 1 hr at −70° C., then cooled to −100° C., and 8.35 mL (8.35 mmol) of 1M ZnCl2 in THF was added. The resulting mixture was slowly warmed to room temperature, stirred for 12 hr at this temperature, and then 1.45 g (7.75 mmol) of 2-bromoanisole and 85 mg (0.15 mmol) of Pd(PtBu3)2 were added. The resulting mixture was refluxed for 3 hr, and then 5 mL of water was added. This mixture was passed through short layer of silica gel 60 (40-63 um) which was then additionally washed with 30 mL of dichloromethane. The combined organic filtrate was evaporated to dryness, and the product was isolated by flash chromatography on silica gel 60(40-63 um, eluent: from hexanes to hexanes-diethyl ether=20:1, vol.). This procedure gave 2.36 g (79%) of the title product.

1. temperaturecooled to −100° C.
2. temperatureThe resulting mixture was slowly warmed to room temperature
3. stirringstirred for 12 hr at this temperature
4. temperatureThe resulting mixture was refluxed for 3 hr
5. washwas then additionally washed with 30 mL of dichloromethane
6. customThe combined organic filtrate was evaporated to dryness
7. customthe product was isolated by flash chromatography on silica gel 60(40-63 um, eluent: from hexanes to hexanes-diethyl ether=20:1, vol.)

ORD record

ord-48ce2117ca204564bb083007c42e29cc

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08541522B2