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

Temperature

-78 °C

To a solution of LDA (8.66 mL, 2M in heptane/THF/ethylbenzene, 17.3 mmol) in 30 mL THF at −78° C., was added a solution of ethyl 4-bromophenylacetate (4.00 g, 16.5 mmol) in 20 mL THF. The mixture was stirred at −78° C. for 30 min, then a solution of iodomethane (10.7 mL, 2M in methyl tert-butyl ether, 21.5 mmol) was added. The mixture was stirred for 10 min at −78° C., then was removed from the cooling bath and stirred for 30 min. The reaction was quenched with sat. NH4Cl, then diluted with EtOAc. The organic phase washed with water, sat. Na2SO3 and brine, dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (0 to 10% EtOAc/hexanes gradient) to afford 3.07 g of 73A as a colorless oil. MS (ESI) m/z 257.1, 259.1 (M+H)+.

1. stirringThe mixture was stirred for 10 min at −78° C.
2. customwas removed from the cooling bath
3. stirringstirred for 30 min
4. customThe reaction was quenched with sat. NH4Cl
5. additiondiluted with EtOAc
6. washThe organic phase washed with water, sat. Na2SO3 and brine
7. dry with materialdried (Na2SO4)
8. concentrationconcentrated
9. customThe crude product was purified by flash chromatography (0 to 10% EtOAc/hexanes gradient)

ORD record

ord-90944d6a01f6450f8f617a10744ef6b5

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07592331B2