Hydrochloric Acid → HCID 57443330, compound

Participants

Reaction Steps

The mixture of 2-bromo-4-methyl-benzoic acid (9.5 g, 32.3 mmol), THF (30.0 mL), and 5.0 M NaOH (26 mL, 129 mmol) is stirred at room temperature overnight. The mixture is acidified with 5.0 M HCl and is extracted with EtOAc (80 mL). The organic phase is washed with brine (60 mL) and is dried (Na2SO4). After filtration, the filtrate is concentrated under reduced pressure to a residue. The residue is dissolved in CH2Cl2 (50 mL) and MeOH (50 mL) and is treated with 2.0 M TMSCHN2 in hexane (30 mL, 60 mmol) at 0° C. for 1.0 h. The reaction mixture is concentrated to a residue and the residue is purified by flash chromatography to afford the title compound as a solid (2.3 g, 29%). LC-ES/MS m/e 247.0 (M+1).

Provenance & Evidence