Dimethylformamide → HCID 59855504, compound

Participants

Reaction Steps

A solution of 3-thiolpropanoic acid methyl ester (1.2 g, 10 mmol) and 4-bromobenzyl-bromide (2.5 g, 10 mmol) in DMF (20 mL) was cooled to 0° C. and treated with Cs2CO3 (3.9 g, 12 mmol). After stirred for 2 h, the reaction was quenched with 5% HCl (25 mL) and diluted with ethyl acetate (50 mL). After seperation, the aqueous layer extracted with ethyl acetate (3×15 mL). The combined organic layers were washed with sat. aq NaCl, dried over MgSO4 and concentrated. Purification by flash column chromatography (2-5% ethyl acetate in heptane) provided 3-(4-bromophenylmethylsulfanyl)-propanoic acid methyl ester (2.5 g, 87%) as white solid. 1H NMR (CDCl3), 7.43 (d, J=8 Hz, 2H), 7.20 (d, J=8 Hz, 2H), 3.68 (s, 5H), 2.67 (m, 2H), 2.56 (t, J=6 Hz, 2H).

Provenance & Evidence