Hydrochloric Acid → HCID 70815867, compound

HRID 1843016Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][S:9]([CH3:12])(=[O:11])=[O:10])=[C:4]([F:13])[CH:3]=1.Cl[CH:15]([CH3:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17].Cl>CN(C)C=O.FC(F)(F)C(O)=O.[Mn]>[F:13][C:4]1[CH:3]=[C:2]([CH:15]([CH3:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:7]=[CH:6][C:5]=1[CH2:8][S:9]([CH3:12])(=[O:11])=[O:10]

Participants

Conditions

Temperature: 60 °C

Procedure

To a stirred solution of 4-bromo-2-fluoro-1-(methylsulfonylmethyl)benzene (2 g, 7.487 mmol) in dimethylformamide (11 mL) were added ethyl 2-chloropropionate (1.24 mL, 9.733 mmol), manganese (822 mg, 14.974 mmol) and (2,2′-bipyridine)nickel(II)-dibromide (196 mg, 0.524 mmol). Trifluoroacetic acid (4 drops) was added. The reaction mixture was stirred overnight at 60° C. After cooling down to room temperature, the mixture was hydrolyzed by 1N HCl (30 mL) and extracted with ethyl acetate (3×50 mL). The organic layer was dried over magnesium sulfate and filtered. The solvent was removed in vacuo. The crude product was purified by CC (eluent: ethyl acetate/cyclohexane (1:1)) to give ethyl 2-(3-fluoro-4-(methylsulfonylmethyl)phenyl)propanoate (966 mg, 45%).

Workup

temperatureAfter cooling down to room temperature
extractionextracted with ethyl acetate (3×50 mL)
dry with materialThe organic layer was dried over magnesium sulfate
filtrationfiltered
customThe solvent was removed in vacuo
customThe crude product was purified by CC (eluent: ethyl acetate/cyclohexane (1:1))

Sources & evidence

ORD record: ord-f86bb2dd99074558b701310666cac967
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946204B2

Reaction notes

Loading…