40733-98-0

Upstream product

• 118268-18-1 C₁₆H₁₈FNO₃S 
• 637-69-4 4-Methoxystyrene 
• 73744-44-2 2-fluoro-4'-methoxyacetophenone 
• 2632-13-5 2-Bromo-4'-methoxyacetophenone 
• 123-11-5 4-methoxy-benzaldehyde 
• 75-05-8 acetonitrile 

Downstream Products

• 130728-26-6 1-(4-methoxyphenyl)-2-fluoroethyl pentafluorobenzoate 
• 1073056-07-1 (R)-2-fluoro-1-(4-methoxyphenyl)ethanol 
• 1073056-13-9 (S)-2-fluoro-1-(4-methoxyphenyl)ethyl benzoate 
• 130728-24-4 1-(4-methoxyphenyl)-2-fluoroethyl chloride 

Relevant academic research and scientific papers

Synthesis of enantiopure fluorohydrins using alcohol dehydrogenases at high substrate concentrations

The use of purified and overexpressed alcohol dehydrogenases to synthesize enantiopure fluorinated alcohols is shown. When the bioreductions were performed with ADH-A from Rhodococcus ruber overexpressed in E. coli, no external cofactor was necessary to obtain the enantiopure (R)-derivatives. Employing Lactobacillus brevis ADH, it was possible to achieve the synthesis of enantiopure (S)-fluorohydrins at a 0.5 M substrate concentration. Furthermore, due to the activated character of these substrates, a huge excess of the hydrogen donor was not necessary.

Asymmetric reduction using (R)-MeCBS and determination of absolute configuration of para-substituted 2-fluoroarylethanols

The asymmetric reduction of eight α-fluoroacetophenones has been investigated using (R)-MeCBS as a catalyst in various media. Based on a solvent screen, 1,2-dimethoxyethane, diethyl ether and dichloromethane were used in reductions of the α-fluoroacetophe

Effect of reaction conditions on the kinetic and activation parameters for the mild introduction of fluorine into α-substituted styrenes with AccufluorTM NFTh

Kinetic studies on fluorination of α-substituted styrenes with 1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (AccufluorTM NFTh) in acetonitrile or in acetonitrile in the presence of methanol or water as nucleophiles were carried out. These reactions exhibited overall second-order kinetics and formed Markovnikov type products. The corresponding second-order rate constants for fluorination of the studied substrates in the presence of methanol at 38.8 deg C are k2 = 1.1 x 10-3 M-1 s-1 for styrene (1a), 3.3 x 10-2 M-1 s-1 for α-methylstyrene (1b) and 3.4 x 10-2 M-1 s-1 for 1,1-diphenylethene (1c). The substitution of methanol as nucleophile by water had very little effect on the rate of the process. Solvent polarity variation (Grunwald-Winstein Ybenzyl) showed a similar small effect, too, indicating negligible change in the polarity of the rate-determining transition state in comparison with the reactants. Activation enthalpies (between 62 and 80 kJ mol-1) and activation antropies (between -74 and 32 J mol-1 K-1) were determined for fluorination of α-substituted styrenes with NFTh in acetonitrile in the presence of methanol and water as nucleophiles. Hammett correlation analysis of the reaction of substituted styrenes with NFTh in MeCN MeCN-H2O and MeCN-MeOH gave reaction constants ρ+ of -1.48, -1.52 and -1.80, respectively, which support our belief in the mainly non-polar character of the rate-determining transition state of the studied reactions.

α-FLUOROMETHYL-N-METHYL-PHENYLSULPHOXIMINE: A NEW FLUOROMETHYLENATION REAGENT

Treatment of aldehydes or ketones with the anion derived from α-fluoromethyl-N-methyl-phenylsulphoximine produces adducts which afford fluoro-olefins on reductive elimination.