Ethyl Bromide → HCID 15506059, compound

Participants

Reaction Steps

Methyl 3-hydroxyphenylacetate (132.5 g, 0.80 mole) was added dropwise to a suspension of 50% NaH (43.2 g, 0.90 mole) in DMF (ie) at 0° C. under N2. The solution was stirred 1 hour at room temperature, cooled in an ice bath, and ethyl bromide (120 ml, 1.6 mole) added. The reaction mixture was stirred overnight at room temperature, filtered, and concentrated in vacuo. A solution of the residue in diethyl ether was washed with dilute NaOH solution and saturated NaCl, dried (Na2SO4) and concentrated in vacuo. The residue was purified by chromatography on silica gel eluting with ethyl acetate:hexane (1:39→1:9) to give methyl 3-ethoxyphenylacetate (94.9 g). 1H NMR (DMSO-d6, 200 MHz) δ: 1.30 (t, J=7 Hz, 3H, ethylCH3), 3.59 (s, 3H, esterCH3), 3.61 (s, 2H, ArCH2), 3.98 (q, J=7 Hz, 2H, ethylCH2), 6.78-6.81 (m, 3H), 7.16-7.24 (m, 1H).

Provenance & Evidence