2,2,2-Trifluoroethanol → HCID 86668529, compound

Participants

Reaction Steps

To a solution of 2,2,2-trifluoroethanol (109 μL, 1.50 mmol) in DMF (2.63 mL) was added NaH (64 mg, 1.6 mmol). The mixture was stirred at room temperature for 1 h before methyl 3-chloro-4-(dibromomethyl)benzoate (342 mg, 1.00 mol) was added. The mixture was stirred at room temperature for 2 h before it was poured into water and was extracted with EtOAc (3×). The organics were combined, washed with water, brine, dried (Na2SO4) and evaporated to dryness. The material was taken up in MeOH and powdered NaOH (160 mg, 4.00 mol) was added and the mixture was stirred at room temperature for 1 h. The mixture was evaporated and treated with 1N HCl (until the solution was strongly acidic). The precipitated product was washed with water and dried to give 4-(bis(2,2,2-trifluoroethoxy)methyl)-3-chlorobenzoic acid. ESI-MS m/z calc. 394.4, found 394.5 (M+1)+; Retention time: 1.74 minutes (3 min run).

Provenance & Evidence