Hydrochloric Acid → Ethyl 2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)propanoate
Reaction equation
Br[C:2]1[CH:13]=[CH:12][C:5]([CH2:6][NH:7][S:8]([CH3:11])(=[O:10])=[O:9])=[C:4]([F:14])[CH:3]=1.[CH2:15]([O:17][C:18](=[O:22])[CH:19](Cl)[CH3:20])[CH3:16].FC(F)(F)C(O)=O.Cl>CN(C)C=O.[Mn]>[F:14][C:4]1[CH:3]=[C:2]([CH:19]([CH3:20])[C:18]([O:17][CH2:15][CH3:16])=[O:22])[CH:13]=[CH:12][C:5]=1[CH2:6][NH:7][S:8]([CH3:11])(=[O:10])=[O:9]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 65 °C
Procedure
N-(4-bromo-2-fluorobenzyl)methanesulfonamide (29 g, 102.8 mmol) and ethyl-2-chloropropionate (18.26 g, 133.6 mmol) were dissolved in dimethylformamide (155 mL) in a protective gas atmosphere at room temperature. Subsequently, manganese (11.29 g, 205.6 mmol), (2,2′-bipyridine)nickel(II) dibromide (2.69 g, 7.2 mmol) and trifluoroacetic acid (1.48 mL) were added and the mixture was stirred at 65° C. for 36 h. The reaction mixture was cooled to room temperature, hydrolysed using 1 N HCl (50 mL) and extracted with diethyl ether (4×100 mL). The combined organic layer were washed with water (40 mL) and brine solution (40 mL) and dried over magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by column chromatography (eluent: diethyl ether/n-hexane 9:1) to afford ethyl 2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)propanoate (12.27 g, 39%).
Workup
- temperatureThe reaction mixture was cooled to room temperature
- extractionextracted with diethyl ether (4×100 mL)
- washThe combined organic layer were washed with water (40 mL) and brine solution (40 mL)
- dry with materialdried over magnesium sulfate
- customThe solvent was evaporated under reduced pressure
- customthe obtained residue was purified by column chromatography (eluent: diethyl ether/n-hexane 9:1)
Sources & evidence
- ORD record
- ord-de3d54fd924a4b7fbd8702fe252758fd
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08937092B2
Reaction notes
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