Carbon Dioxide → 1-Chloro-4-[2,3,3-trifluoro-1-(2-methoxyethyl)-2-propenyl]benzene

Temperature

60 °C

Bromotrifluoroethylene (41.5 g, 257 mmol) was distilled (dry ice condenser) into a flask containing zinc (13.6 g, 208 mmol) and N,N-dimethylformamide (153 ml), and the resulting mixture was heated at approximately 60° C. for two hours. The reaction mixture was purged with nitrogen for one hour, cooled to −8° C., treated with cuprous bromide (29.83 g, 208 mmol), and stirred for 30 minutes without external cooling. 3-(4-chlorophenyl)-3-bromopropyl methyl ether (17.06 g, 64.7 mmol) in N,N-dimethylformamide (10 ml) was added followed by limonene (5 drops), and the resulting mixture was heated at 50° C. for 8 hours. The cooled reaction mixture was quenched with aqueous ammonium chloride and thoroughly extracted with hexane. The combined organic extracts were dried over anhydrous sodium sulfate and concentrated in vacuo to a brown oil (10.76 g). Chromatography on silica gel eluting with methylene chloride:hexane (1:9) afforded the title compound as a yellow oil (2.25 g), which was characterized by IR, 1HNMR and mass spectral analysis.

1. customThe reaction mixture was purged with nitrogen for one hour
2. temperaturecooled to −8° C.
3. temperaturethe resulting mixture was heated at 50° C. for 8 hours
4. customThe cooled reaction mixture
5. customwas quenched with aqueous ammonium chloride
6. extractionthoroughly extracted with hexane
7. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
8. concentrationconcentrated in vacuo to a brown oil (10.76 g)

ORD record

ord-e561f314e7744366a11168dbac168c4f

Source dataset

uspto-grants-2003_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06506800B2