Acetic Acid → Acetic Acid 2-(4-bromomethyl-6-chloro-pyrimidin-5-yl)-ethyl ester

Participants

Reaction Conditions

Reaction Steps

Br2 (1.4 g, 8 mmol) is added drop wise to a stirred solution of 5-(2-benzyloxy-ethyl)-4-chloro-6-methyl-pyrimidine (2.1 g, 8 mmol) in HOAc (20 ml) at 85° C. After addition, the mixture is stirred at 85° C. for an additional 1 hour. The solvent is removed in vacuo and EtOAc (25 ml) and NaHCO3 (25 ml) are added to the residue. The layers are separated and the organic layer is washed with Na2S2O3 solution (sat. 15 ml) followed by brine (20 ml). The organic phase is dried (Na2SO4) and solvent evaporated. The resulting yellow oil is purified by flash column (EtOAc:hexane=6:1) to afford 5-(2-benzyloxy-ethyl)-4-bromomethyl-6-chloro-pyrimidine as a light yellow solid and acetic acid 2-(4-bromomethyl-6-chloro-pyrimidin-5-yl)-ethyl ester (162).

Provenance & Evidence