Methyl iodide → Ethyl 2-(4-bromophenyl)propanoate

Temperature

-78 °C

To ethyl 4-bromophenylacetate (2.137 g, 8.8 mmol) in THF (20 mL) at −78° C. was added lithium bis(trimethylsilyl)amide (1M in hexane; 11.4 mL, 11.4 mmol), and the solution was stirred for 1 hour at −78° C. Iodomethane (0.71 mL, 11.4 mmol) in THF (5 mL) was added, and the reaction was warmed to room temperature. The mixture was quenched with water and concentrated. The residue was dissolved in EtOAc and washed three times with water and once with brine. The organic layer was dried and concentrated, and the crude material was purified by silica gel chromatography (0-60% EtOAc in hexanes) to give 2-(4-bromo-phenyl)-propionic acid ethyl ester.

1. temperaturethe reaction was warmed to room temperature
2. customThe mixture was quenched with water
3. concentrationconcentrated
4. dissolutionThe residue was dissolved in EtOAc
5. washwashed three times with water
6. customThe organic layer was dried
7. concentrationconcentrated
8. customthe crude material was purified by silica gel chromatography (0-60% EtOAc in hexanes)

ORD record

ord-ccb44128d50c415791505999bebeb704

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08440707B2