3- Nitrophenyl trifluoromethyl ether

Nitrophenyl trifluoromethyl ether has been derived in 62% yield from a vigorously stirred mixture of 3-nitrophenol, anhydrous carbon tetrachloride and antimony pentafluoride together with a little antimony pentachloride by heating at 150°C for 5.5 hours (ref.73). 

FIG. 9 Differential capacity C of the interface between 0.1 M LiCl in water and 0.02 M tetrabu-tylammonium tetraphenylborate ( ) or tetrapentylammonium tetrakis[3,5-bis(trifluoromethyl)phe-nyl]borate ( ) in o-nitrophenyl octyl ether as a function of the interfacial potential difference (From Ref 73.)... 

The membrane of these EPMEs contain 1.2% chiral selector, 65.6% ortho-nitrophenyl octyl ether (o-NPOE) or dioctylsebacate (DOS) (plastifiant), 0.4% tetrakis([3,5-bis(trifluoromethyl)phenyl]borate) (TKB) in a tetra-hydrofuran solution containing the PVC (32.4% from the membrane composition) [37,42]. A 7-mm diameter circle was cut from the membrane and inserted into a electrode body along with a inner solution containing the enantiomer to be determined in a certain concentration (usually 1CT3 mol/L). 

Poly(vinyl chloride) (PVC) with an average polymerization degree of 1100 was purified by reprecipitation from THF in methanol. The plasticizers or membrane solvents, di-n-octylphthalate (DOP), o-nitrophenyl octyl ether (NPOE), and 2-fluorophenyl-2-nitrophenyl ether (FPNPE) were obtained from Dojindo Laboratories. The lipophilic salt, sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate (NaTFPB), was obtained from Tokyo Chemical Industry Co., Ltd. and Dojindo Laboratories. 

Rohm and Haas introduced recently two new members of the diphenyl ether group, namely 5-(2-chloro-4-trifluoromethyl)phenoxy-2-nitrobenzoic acid (acifluorfen, 4) and 2-chloro-4-(trifluoromethyl)phenyl 3-ethoxy-4-nitrophenyl ether (oxyfluorfen, 5) (Biroli et al., 1980 Theissen, 1982 Swithenbank, 1982). Acifluorfen is used as its sodium salt soluble in water. 

Synonyms 2-Chloro-1-(3-ethoxy4-nitrophenoxy)-4-(trifluoromethyl) benzene 2-Chloro-4-(trifluoromethylphenyl) 3-ethoxy-4-nitrophenyl ether Ether, 2-chloro-a,a,a-trifluoro-p-tolyl 3-ethoxy-4-nitrophenyl Empirical C1SH11CIF3NO4 Properties M.w. 361.72... 

The substrate scope was found to be very similar to that described above for the 4-nitrophenyl esters, although the selectivity for the hnear alkene products in the Mizoroki-Heck reaction was somewhat lower. The reaction tolerates many functionalities, including esters, ethers, nitro, keto, trifluoromethyl and even formyl groups (Table 4.1). 

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