Methyl iodide → 2-(3-Bromo-5-chloro-phenyl)-propionic acid ethyl ester

HRID 1810582Notes

Reaction equation

HRID 1810582 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[CH2:5][C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]([Br:13])[CH:7]=1)[CH3:2].[H-].[Na+].IC.[CH3:19]COC(C)=O>CN(C=O)C.O>[CH2:1]([O:3][C:4](=[O:14])[CH:5]([C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]([Br:13])[CH:7]=1)[CH3:19])[CH3:2]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 58149300HCID 58149300, compound

Product 1

HCID 574588072-(3-Bromo-5-chloro-phenyl)-propionic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (3-bromo-5-chloro-phenyl)-acetic acid ethyl ester (5.0 g, 18.0 mmol) in DMF (50 mL) at 0° C. under N2 was added sodium hydride (60% in mineral oil; 0.8 g, 19.8 mmol), and the mixture was warmed to room temperature over 15 minutes. Iodomethane (1.3 mL, 19.8 mmol) was added, and the reaction was monitored by analytical LCMS. Once the reaction was complete, the mixture was worked-up with EtOAc and H2O, and the crude material was purified by silica gel chromatography to give the title compound.

Workup

  1. customthe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-1bfb0005bec2496da9147529942b0e74
Source dataset
uspto-grants-2013_01
Patent number
US08362044B2

Reaction notes

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