22102-10-9

Usage

InChI:InChI=1/C10H9F3O2/c1-15-8-4-2-7(3-5-8)6-9(14)10(11,12)13/h2-5H,6H2,1H3

Upstream product

• 104-01-8 4-Methoxyphenylacetic acid 
• 383-63-1 ethyl trifluoroacetate, 
• 407-25-0 trifluoroacetic anhydride 
• 4693-91-8 4-methoxyphenyl-acetic chloride 

Downstream Products

• 161809-70-7 (Z)-3-Chloro-4,4,4-trifluoro-2-(4-methoxy-phenyl)-but-2-enal 
• 1620100-57-3 C₂₀H₁₇F₃O₃ 
• 1602864-52-7 (3S,4R)-4-(4-bromophenyl)-1,1,1-trifluoro-3-(4-methoxyphenyl)-5-nitropentan-2-one 
• 1324825-79-7 2,2,2-trifluoro-1-[2-(4-methoxybenzyl)phenyl]ethanone 

Relevant academic research and scientific papers

Access to substituted trifluoromethyl ketones using the versatile synthetic intermediate (E)-1,1-dimethyl-2-(1,1,1-trifluoropropan-2-ylidene)hydrazine

The N,N-dimethylhydrazone of 1,1,1-trifluoroacetone, (E)-1,1-dimethyl-2-(1,1,1-trifluoropropan-2-ylidene)hydrazine, has been shown to undergo a diverse set of reactions following deprotonation with n-butyl-lithium; including alkylation, addition to ketones and aldehydes, as well as palladium-catalyzed cross-couplings with aryl bromides. Mild hydrolysis of the N,N-dimethylhydrazone products from these transformations affords the corresponding trifluoromethyl ketones in good to excellent yields.

Highly efficient synthesis of chiral α-CF3 amines via Rh-catalyzed asymmetric hydrogenation

Highly enantioselective catalytic asymmetric hydrogenation of α-CF3-enamides has been achieved by employing rhodium-DuanPhos as the catalyst, which provides a readily accessible method for the synthesis of chiral trifluoromethylated amines. The reaction has a broad substrate scope; both aryl- and alkyl-substituted α-CF3-enamides worked smoothly and afford the corresponding chiral amines in high yields and excellent enantioselectivities (up to 99% ee).

Exalted resonance demands in the substituent effects on the acetolyses of 2-arylethyl trifluoromethanesulfonates destabilized by cn and cf3 groups

Substituent effects on the acetolysis rates of 2-aryl-l-cyano-l- (trifluoromethyl)ethyl trifluoromethanesulfonates (α-OTf) and 2-aryl-2-cyano-2-(trifluoromethyl)ethyl trifluoromethanesulfonates (ss-OTf) were investigated by using LArSR equation. The obtained p and r+ values were p = -3.28, r+ = 0.98 and p = -3.48,r+ = 0.93 for the acetolysis of α-OTf and ss-OΥi, respectively. The obtained p values are comparable to those for typical aryl-assisted solvolyses, but the r+ values are much larger. The large r+ values suggest that the ester bond cleavages in the deactivated aryl-assisted solvolyses are assisted by the strong participation of the ss-aryl group.

Trifluoromethyl ketones from enolizable carboxylic acids via enediolate trifluoroacetylation/decarboxylation

(Chemical Equation Presented) Primary and secondary (enolizable) carboxylic acids were converted in a single step to trifluoromethyl ketones. Treatment of the acid with 2.2 equiv of LDA generated an enediolate that was trifluoroacetylated with EtO2CCF3. Quenching the reaction mixture with aqueous HCl resulted in rapid decarboxylation and provided the trifluoromethyl ketone product in good yield. The process may be performed at -20°C with a slight reduction in yield. The reaction was extended to the preparation of pentafluoroethyl and chlorodifluoromethyl ketones.