1-(2,6-Dichloro-3-fluorophenyl)ethanone → (S)-1-(2,6-dichloro-3-fluorophenyl)ethanol

HRID 705404Notes

Reaction equation

CC(C)([O-])C.[K+].[Cl:7][C:8]1[C:13]([F:14])=[CH:12][CH:11]=[C:10]([Cl:15])[C:9]=1[C:16](=[O:18])[CH3:17].[H][H]>CC(O)C>[Cl:7][C:8]1[C:13]([F:14])=[CH:12][CH:11]=[C:10]([Cl:15])[C:9]=1[C@@H:16]([OH:18])[CH3:17]

Participants

Conditions

Temperature: 40 °C

Procedure

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.

Workup

customwhile measuring with syringe

Sources & evidence

ORD record: ord-b7ef13b485b54accaeff57b5746530a0
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174906B2

Reaction notes

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