ChemicalBook CAS DataBase List (S)-2-CHLORO-1-(4-FLUOROPHENYL)ETHANOL

(S)-2-CHLORO-1-(4-FLUOROPHENYL)ETHANOL synthesis

9synthesis methods

Product Name:(S)-2-CHLORO-1-(4-FLUOROPHENYL)ETHANOL
CAS Number:126534-42-7
Molecular formula:C8H8ClFO
Molecular Weight:174.6

108-05-4
562 suppliers
$4.00/1000g

61592-48-1 Synthesis

61592-48-1
13 suppliers
inquiry

Benzenemethanol, α-(chloromethyl)-4-fluoro-, 1-acetate, (αS)-

134295-34-4
0 suppliers
inquiry

126534-42-7
48 suppliers
inquiry

126534-43-8
59 suppliers
inquiry

Yield:99 % ee ， 82 % ee

Reaction Conditions:

with Amano AK lipase from Pseudomonas fluorescens immobilized on silk friboin-alginate sphere in hexane at 32; for 120 h;Resolution of racemate;Enzymatic reaction;enantioselective reaction;

Steps:

Kinetic resolution of chlorohydrins (R,S)-1a-h by immobilized lipase from P. fluorescens

General procedure: To a 3 mL vial flask were added HPLC grade solvent(1 mL), vinyl acetate (0.100 mL), immobilized lipase Fib-Alg (30mg) and the appropriate chlorohydrins (R,S)-1a-h (40 mg). The reaction mixture was stirred in a mechanic agitation at 300 rpm, at 32 C. The progress of the reactions was followed by removing samples (30 μL of reaction mixture were added to 600 μL of EtOAc) for GC or HPLC analyses, according to the time indicated in Table 4. After the reaction was complete, the immobilized lipase was filtered off. The filtrate was evaporated under reduced pressure and purified by column chromatography on silica gel using hexanes/EtOAc (8:2) as eluent, yielding the enantiomerically enriched (R)-alcohols 1a-h and (S)-acetates 2a-h.

References:

Ferreira, Irlon M.;Nishimura, Rodolfo H.V.;Souza, Ana B. Dos A.;Clososki, Giuliano C.;Yoshioka, Sergio A.;Porto, André L.M. [Tetrahedron Letters,2014,vol. 55,# 36,p. 5062 - 5065] Location in patent:supporting information