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

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 4-bromophenylacetate (2 g, 8.23 mmol) in anhydrous DMF (20 ml) was carefully added NaH (60% in mineral oil, 0.494 g, 12.34 mmol) at 0° C. (ice bath). The resulting slurry was stirred at 0° C. for 30 min, then MeI (0.643 ml, 10.28 mmol) was added and the reaction mixture was allowed to warm to RT and further stirred for 1 h. A saturated aqueous NH4Cl solution was added to quench the reaction and the mixture was extracted with AcOEt (2×). The combined organic fractions were dried over Na2SO4, filtered and evaporated to dryness. The resulting crude material was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, heptane/AcOEt 99:1 to 8:2) to yield the title compound (777.8 mg, 3.03 mmol, 37% yield) as a colorless oil. TLC: RF=0.64 (heptane/AcOEt 3:1); HPLC: AtRet=2.60 min; 1H NMR (400 MHz, DMSO-d6): 1.13 (t, J=7.1, 3H), 1.37 (d, J=7.1, 3H), 3.79 (q, J=7.1, 1H), 3.98-4.12 (m, 2H), 7.22-7.28 (m, 2H), 7.49-7.56 (m, 2H).

Provenance & Evidence