Hydrochloric Acid → HCID 69135125, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of dithiocarbonic acid O-ethyl ester S-(2-trifluoromethyl-biphenyl-4-yl) ester (128 mg, 0.3738 mmol) in EtOH (5 mL) is added aqueous NaOH (1 N, 5 mL). The mixture is heated at 65° C. for 3 h. After cooling to room temperature, 1 N HCl (aq) is added until the reaction pH is adjusted to ca. pH=5. The reaction is diluted with EtOAc and washed with H2O followed by saturated aqueous NaCl. The organic solution is dried over Na2SO4. After concentration, the crude 2-trifluoromethyl-biphenyl-4-thiol product obtained (64 mg, 0.2519 mmol) is dissolved in EtOH (5 mL). NaBH4 (19 mg, 0.5039 mmol, 2 eq.) is added to this solution. The resulting mixture is stirred at room temperature for 25 min at which point methyl-4-(bromomethyl)benzoate (58 mg, 0.2519 mmol, 1 eq.) in DMF (1.5 mL) is added to the reaction. The mixture is stirred at room temperature an additional 30 min. The EtOH is removed under vacuum. The resulting DMF solution is diluted with EtOAc and washed with H2O followed by saturated aqueous NaCl. The organic solution is dried over Na2SO4. After concentration, the residue is purified by silica gel chromatography (3:1 hexanes/EtOAc) to give 4-(2-trifluoromethyl-biphenyl-4-ylsulfanylmethyl)-benzoic acid methyl ester. [MS: (ES+) 425.1 (M+23)+].

Provenance & Evidence