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

Temperature

-78 °C

A solution of methyl 2-(4-bromophenyl)acetate, 7-d, (1.0 g, 4.4 mmol) in THF (5 mL) was cooled to −78° C. under nitrogen, and slowly treated with LDA (2 M in THF, 2.2 mL, 4.4 mmol) at −78° C. The resulting mixture was stirred at −78° C. for 30 min, and then a solution of iodomethane (0.6 g, 4.4 mmol) in THF (10 mL) was added dropwise and the mixture was stirred at −78° C. for another 30 min and then warmed up slowly to room temperature and stirred overnight. The reaction mixture was concentrated and then crush ice was added. Then the mixture was added saturated aqueous ammonium chloride (10 mL) and extracted by EA. Combined organic layers were washed with brine, dried over Na2SO4 and concentrated. The residue was purified by column chromatography to give the title compound, 7-e, (650 mg, 61%). 1H NMR (300 MHz, CDCl3) δ1.49 (d, J=7.2 Hz, 2H), 3.67-3.72 (m, 4H), 7.17 (d, J=8.4 Hz, 2H), 7.44 (d, J=8.4 Hz, 2H). LC-MS (M+H)+ 243, 245.

1. stirringthe mixture was stirred at −78° C. for another 30 min
2. temperaturewarmed up slowly to room temperature
3. stirringstirred overnight
4. concentrationThe reaction mixture was concentrated
5. additioncrush ice was added
6. additionThen the mixture was added saturated aqueous ammonium chloride (10 mL)
7. extractionextracted by EA
8. washCombined organic layers were washed with brine
9. dry with materialdried over Na2SO4
10. concentrationconcentrated
11. customThe residue was purified by column chromatography

ORD record

ord-2238ffd1b85f4c489da38eeff1cf3e5b

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09079930B2