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In 1,2-dichlorotrifluoroethyl-trifluoromethylether; at -40℃;Inert atmosphere;
General procedure: The procedure consists of bubbling a stream of hypofluorite (5.5 NL/h: He = 80%, FTM = 18.5%, COF2 = 1.5%) into a solution of the aromatic compounds maintained at the desired temperature (-30 C; -80 C) in a semi-batch method [57].The solubility of the aromatic compounds was measured by carrying out a cloud-point measurement in selected solvents. All the aromatics tested (alpha,alpha,alpha-trifluoro-toluene, toluene, benzene, chloro-benzene, methoxybenzene) are soluble at concentrations between 4% and 5% in the chloro-fluoro-ether (CF3OCFClCF2Cl) used as reaction solvent.A cylinder containing 150 ml of a diluted (3%) solution of the aromatic substrate in 1,2-dichlorotrifluoroethyl-trifluoromethyl-ether (CF3OCFClCF2Cl) was prepared at room temperature. This solution was then poured in the 250 ml stainless steel stirred reactor, cooled at -40 C and then stripped with helium for 15 min to eliminate the dissolved air since oxygen strongly interacts with radical based mechanisms.Subsequently the hypofluorite stream was bubbled in the reactor kept at -40 C under vigorous mechanical stirring. For one mole of aromatic substrate only 0.05-0.88 mol of hypofluorite were added, obtaining only a partial conversion of the aromatics.
2-chloro-6-(trifluoromethoxy)benzaldehyde[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
99%
N,N-Di-isopropylamine (38.4 ml, 27lmmol) was added dropwise to a solution of nbutyllithium (1.6 M, 169 ml, 271 mmol) in THF (180 ml) at 0C and the reaction mixture was stirred and allowed to warm to room temperature over 30 mins. The LDA solution was then added drop wise over lOminutes to a solution of 1-chloro-3- (trifluoromethoxy)benzene (50 g, 246 mmol) in THF (500 ml) at -70C and the resultingmixture was stirred at -70C for 30 minutes. Finally N,N-dimethylformamide (23 ml, 296 mmol) was added dropwise and the resultant mixture stirred at -70C for 30 minutes.The reaction was quenched at -70C by addition of NH4C1 (saturated aqueous solution) to pH 7-8 and the resulting mixture was extracted with EtOAc (3 x 75 ml). The combined organic phases were washed with water (100 ml), brine (100 ml), dried over magnesium sulfate, filtered and concentrated under reduced pressure to provide the title compound (55 g, 99% yield).LCMS (Method 16, ES+) RT 1.32 mm., 224 [M+H].
1-chloro-2-iodo-3-(trifluoromethoxy)benzene[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
96%
To a cooed (-78 C) soution of 1-choro-3-(trifluoromethoxy)benzene (100 g, 510 mmo)in THF (500 mL) was added n-butyflithium (2.5 M/hexanes, 205 mL, 510 mmo)dropwise over a period of 10 minutes. Stirring was maintained at -78 C for I h, andthen a soution of iodine (130 g, 510 mmo) in THF (500 mL) was added dropwise at -78C over a period of 30 minutes. After the addition, the temperature was maintained at -78 C for lh and then aflowed to warm to rt and stirred for a tota? of 18h. The reaction mixture was poured into saturated aqueous Na2SO3 and extracted with EtOAc (2 x 1000 mL). The combined organic extracts were dried over Na2SO4 and concentrated in vacuo to give the tifle compound as an oH (159 g, 96% yied). 1H NMR (500 MHz, CDC3) 67.40 (dd, J= 8.1, 1.4 Hz. IH), 7.32 (t, J= 8.1 Hz, IH). 7.16(dt. J= 8.2, 1.4 Hz, IH).
85%
To a cooed (-.78 C) souUon of 1-choro-3-(trfluoromethoxy)benzene (20 g, 102 mrno)n THF (100 mL) was added n-butyWthum (2.5 M/hexanes, 41 mL, 102 mmo) dropwseover a period of 10 minutes. Strrng was mantaned at -78C for I h, and then asouDon of odne (26 g, 102 rnrno) n THF (100 mL) was added dropwse at -.78 C overa perod of 30 ninutes. After the add Won, the temperature was niantaned at -78 C for1 h and then aflowed to warm to rt and stirred for a tota of 18 h. The reacton mixturewas poured nto saturated aqueous Na2SO3 and extracted wfth EtOAc (2 x 200 mL). The combined organc extracts were dried over Na2SO4 and concentrated n vacuo to give the tWe compound as an oH (28 g, 85% yed). 1H NMR (500 MHz, CDC3) oe 7.40 (dd, J = 81, 1.4 Hz, IH), 7.32 (t, J = 8.1 Hz, IH), 7.16 (dt, J = 8.2, 1.4 Hz, IH).
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