Triethylsilane → 5-Bromo-3-ethyl-2-hydroxybenzoic acid

Participants

Reaction Conditions

Reaction Steps

974 mg (3.73 mmol) of 5-bromo-2-hydroxy-3-(1-hydroxy-ethyl)-benzoic acid was dissolved in trifluoroacetic acid under nitrogen. 715 μL (521 mg, 4.48 mmol) of triethyl silane was added and the resulting mixture was heated to 90° C. for 2 h. The mixture was evaporated and the residue purified by flash chromatography on silica gel using a gradient of ethyl acetate in hexanes to afford 563 mg (2.30 mmol, 62%) of 5-bromo-3-ethyl-2-hydroxy-benzoic acid as a colorless solid. 1H-NMR (500 MHz, d6-DMSO): δ 7.73 (d, 1H), 7.57 (d, 1H), 2.61 (q, 2H), 1.15 (t, 3H); MS: m/z 243.0+244.9 (M+H+).

Provenance & Evidence