Carbon Dioxide → HCID 59473815, compound

Participants

Reaction Conditions

Reaction Steps

At 0° C., to a solution of iPrMgCl (9.10 mL, 2.0M THF, 1.2 eq.) in THF (14 mL) was added nBuLi (22.3 mL, 1.6 M Hexanes, 2.4 eq.). After 10 min., now yellow, homogeneous solution was cooled to −78° C., and to this was added a solution of (4-Bromo-3-fluoro-5-methyl-phenyl)-dimethyl-amine (3.52 g, 15.2 mmol) in THF (18 mL). Following the disappearance of the yellow color, the TLC after 20 min. showed no starting material. CO2(g) was canula transferred into the reaction mixture, which was warmed to room temperature, after 20 min., and added to 1N NaOH. The aqueous layer was acidified with 1NHCl(aq) and extracted with EtOAc. Organic extracts were dried (MgSO4), filtered, concentrated in vacuo to give a crude solid, which was purified by flash chromatography (SiO2, 40%-100% EtOAc/Hexanes) to give 4-Dimethylamino-2-fluoro-6-methyl-benzoic acid as a white solid (2.91 g, 97%).

Provenance & Evidence