Potassium Carbonate → HCID 10116680, compound

Participants

Reaction Steps

A mixture of 3-(3,5-dibromo-4-hydroxyphenyl)-2-hydroxypropionic acid methyl ester (0.25 mmol) and potassium carbonate (0.3 mmol) in acetonitrile (5 mL) was stirred for 10 minutes at room temperature under nitrogen. 2-Bromomethylnaphthalene (0.3 mmol) dissolved in acetonitrile (1 mL) was added with a syringe. The reaction mixture was stirred for 15 hours at room temperature under nitrogen. After concentration in vacuo, the light yellow residue was diluted with ethyl acetate (20 mL) and washed with brine (25 mL). The organic phase was dried over magnesium sulphate and concentrated in vacuo. The residue was purified on column (ethyl acetate/n-heptane 1:3). The fractions containing the coupled material were pooled, concentrated and dissolved in methanol (10 mL), and an aqueous solution of lithium hydroxide (10 mL, 1N) was added carefully. The reaction mixture was stirred for 15 hours at room temperature, acidified with hydrochloric acid (2 N) and the volatile solvents removed in vacuo. The formed precipitate was collected, washed with water and purified with HPLC (YMC-Pack, D-C8-5, 250×20 mm, 5 μm, 120A; Mobile phase: 40% acetonitrile and 60% 25 mM ammonium acetate). This gave 11 mg (9%) of 3-[3,5-dibromo-4-(naphthalen-2-ylmethoxy)phenyl]-2-hydroxypropionic acid as a white solid mass. LC/MS (electrospray): m/z 479 (M−1).

Provenance & Evidence