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ChemicalBook CAS DataBase List (S)-1-(2,6-Dichloro-3-fluorophenyl)ethanol
877397-65-4

(S)-1-(2,6-Dichloro-3-fluorophenyl)ethanol synthesis

7synthesis methods
(S)-1-(2,6-Dichloro-3-fluorophenyl)ethanol is synthesised using (1S)-1-(2,6-dichloro-3-fluorophenyl)ethyl acetate as a raw material by chemical reaction. The specific synthesis steps are as follows:
Sodium methoxide (19 mmol; 0.5 M in methanol) was added slowly to compound S-2 (4.64 g, 18.8 mmol) under a nitrogen atmosphere at 0° C. The resulting mixture was stirred at room temperature for 4 hours. The solvent was evaporated and H2O (100 mL) was added. The cooled reaction mixture was neutralized with sodium acetate-acetic acid buffer solution to pH 7. Ethyl acetate (100 mL.x.2) was added to extract the aqueous solution. The combined organic layers were dried over Na2SO4, filtered, and evaporated to obtain S-1 as a white solid (4.36 g, 94.9percent yield); SFC-MS: 97percent ee. 1H NMR (400 MHz, chloroform-D) δ ppm 1.65 (d, J=6.8 Hz, 3 H) 5.58 (q, J=6.9 Hz, 1H) 6.96-7.10 (m, 1H) 7.22-7.36 (m, 1H).
(S)-1-(2,6-Dichloro-3-fluorophenyl)ethanol synthesis
290835-85-7 Synthesis
2,6-Dichloro-3-fluoroacetophenone

290835-85-7
266 suppliers
$6.00/10g

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Yield:877397-65-4 100%

Reaction Conditions:

with RuBr2[(S,S)-2,4-bis(diphenylphosphino)pentane](2-aminomethyl-3,5-dimethylpyridine);potassium tert-butylate;hydrogen in isopropyl alcohol at 40; for 21 h;Autoclave;Inert atmosphere;Reagent/catalyst;Concentration;

Steps:

7 The hydrogenating reaction of 2′,6′-dichloro-3′-fluoroacetophenone

In an autoclave, 3.22 mg of RuBr2[(S,S)-xylskewphos](3,5-Me2pica) (3.39×10-3 mmol, S/C=1000) and 7.62 mg of potassium tert-butoxide (6.79×10-2 mmol) are placed, replaced with argon gas. Under argon gas flow, 0.5 mL of 2′,6′-dichloro-3′-fluoroacetophenone (3.39 mmol, from Jiangxi Jixiang Pharmachemical) and 2.9 mL of 2-propanol are added while measuring with syringe, pressurized with hydrogen to 10 atm., stirred at 40° C. for 21 hours, and the reduction of hydrogen pressure was confirmed and (S)-1-(2,6-dichloro-3-fluorophenyl)ethanol was obtained at 100% yield. The optical purity measured by HPLC (DAICEL CHRALPAK AD-RH, acetonitrile/water=25/75, 0.5 mL/min, 25° C., 220 nm, the retention time of each enantiomer: (S): 56.1 min, (R): 64.5 min) was 98.5% ee.

References:

US2015/31920,2015,A1 Location in patent:Paragraph 0168

290835-85-7 Synthesis
2,6-Dichloro-3-fluoroacetophenone

290835-85-7
266 suppliers
$6.00/10g

330156-50-8 Synthesis
(R)-1-(2,6-Dichloro-3-fluorophenyl)ethanol

330156-50-8
178 suppliers
$8.00/1g

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